PRODUCTS

DIMETHYLFORMAMIDE

CAS Number: 68-12-2
EC Number: 200-679-5
Formula: HCON(CH3)2
IUPAC name: N,N-Dimethylformamide

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H.
Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids.
DMF is a common solvent for chemical reactions.
Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine.
Dimethylamine degradation impurities can be removed by sparging degraded samples with an inert gas such as argon or by sonicating the samples under reduced pressure.
As Dimethylformamides name indicates, Dimethylformamide is a derivative of formamide, the amide of formic acid.
DMF is a polar (hydrophilic) aprotic solvent with a high boiling point.
Dimethylformamide facilitates reactions that follow polar mechanisms, such as SN2 reactions.

Applications of Dimethylformamide:
The primary use of DMF is as a solvent with low evaporation rate.
DMF is used in the production of acrylic fibers and plastics.
Dimethylformamide is also used as a solvent in peptide coupling for pharmaceuticals, in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.

Dimethylformamide is used as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction, another useful method of forming aldehydes.
Dimethylformamide is a common solvent in the Heck reaction.
Dimethylformamide is also a common catalyst used in the synthesis of acyl halides, in particular the synthesis of acyl chlorides from carboxylic acids using oxalyl or thionyl chloride.
The catalytic mechanism entails reversible formation of an imidoyl chloride:
Me2NC(O)H + (COCl)2 → CO + CO2 + [Me2N=CHCl]Cl
The iminium intermediate reacts with the carboxylic acid, abstracting an oxide, and regenerating the DMF catalyst.

DMF penetrates most plastics and makes them swell.
Because of this property DMF is suitable for solid phase peptide synthesis and as a component of paint strippers.
DMF is used as a solvent to recover olefins such as 1,3-butadiene via extractive distillation.
Dimethylformamide is also used in the manufacturing of solvent dyes as an important raw material.
Dimethylformamide is consumed during reaction.
Pure acetylene gas cannot be compressed and stored without the danger of explosion.
Industrial acetylene is safely compressed in the presence of dimethylformamide, which forms a safe, concentrated solution.
The casing is also filled with agamassan, which renders Dimethylformamide safe to transport and use.

Proper uses of Dimethylformamide:
Dimethylformamide, as a cheap and common reagent, has many uses in a research laboratory.

Uses of Dimethylformamide:
Dimethylformamide is primarily used as an industrial solvent.
Dimethylformamide solutions are used to process polymer fibers, films, and surface coatings; to permit easy spinning of acrylic fibers; to produce wire enamels, and as a crystallization medium in the pharmaceutical industry.

DMF is effective at separating and suspending carbon nanotubes, and is recommended by the NIST for use in near infrared spectroscopy of such.
DMF can be utilized as a standard in proton NMR spectroscopy allowing for a quantitative determination of an unknown compound.
In the synthesis of organometallic compounds, Dimethylformamide is used as a source of carbon monoxide ligands.
DMF is a common solvent used in electrospinning.
DMF is commonly used in the solvothermal synthesis of Metal–Organic Frameworks.
DMF-d7 in the presence of a catalytic amount of KOt-Bu under microwave heating is a reagent for deuteration of polyaromatic hydrocarbons.

Structure and properties of Dimethylformamide:
As for most amides, the spectroscopic evidence indicates partial double bond character for the C-N and C-O bonds.
Thus, the infrared spectrum shows a C=O stretching frequency at only 1675 cm−1, whereas a ketone would absorb near 1700 cm−1.
DMF is a classic example of a fluxional molecule.

The ambient temperature 1H NMR spectrum shows two methyl signals, indicative of hindered rotation about the (O)C-N bond.
At temperatures near 100 °C, the 500 MHz NMR spectrum of this compound shows only one signal for the methyl groups.
DMF is miscible with water.
The vapour pressure at 20 °C is 3.5 hPa.

A Henry's law constant of 7.47 × 10−5 hPa m3 mol−1 can be deduced from an experimentally determined equilibrium constant at 25 °C.
The partition coefficient log POW is measured to −0.85.
Since the density of DMF (0.95 g cm−3 at 20 °C) is similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.

Reactions of Dimethylformamide:
DMF is hydrolyzed by strong acids and bases, especially at elevated temperatures.
With sodium hydroxide, DMF converts to formate and dimethylamine.
DMF undergoes decarbonylation near Dimethylformamides boiling point to give dimethylamine.

Distillation is therefore conducted under reduced pressure at lower temperatures.
In one of its main uses in organic synthesis, DMF was a reagent in the Vilsmeier–Haack reaction, which is used to formylate aromatic compounds.
The process involves initial conversion of DMF to a chloroiminium ion, [(CH3)2N=CH(Cl)]+, known as a Vilsmeier reagent, which attacks arenes.

Organolithium compounds and Grignard reagents react with DMF to give aldehydes after hydrolysis in a reaction named after Bouveault.
Dimethylformamide forms 1:1 adducts with a variety of Lewis acids such as the soft acid I2, and the hard acid phenol.
Dimethylformamide is classified as a hard Lewis base and its ECW model base parameters are EB= 2.19 and CB= 1.31.
Dimethylformamides relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.

Production of Dimethylformamide:
DMF was first prepared in 1893 by the French chemist Albert Verley (8 January 1867 – 27 November 1959), by distilling a mixture of dimethylamine hydrochloride and potassium formate.
DMF is prepared by combining methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.
Although currently impractical, DMF can be prepared from supercritical carbon dioxide using ruthenium-based catalysts.

Molecular Weight: 73.09
3DMet: B00545
Beilstein Reference: 605365
CHEBI:17741
ChEMBL: ChEMBL268291
ChemSpider: 5993
DrugBank: DB01844
ECHA InfoCard: 100.000.617
EC Number: 200-679-5
KEGG: C03134
MeSH: Dimethylformamide
PubChem CID: 6228
RTECS number: LQ2100000
UNII: 8696NH0Y2X
UN number: 2265
CompTox Dashboard (EPA): DTXSID6020515

Description of Dimethylformamide
Dimethylformamide is an organic solvent for vinyl res ins and acetylene, butadiene and acid gases.
Dimethylformamide caused contact dermatitis in a technician at an epoxy resin manufacturers, and can provoke alcohol-induced flushing in exposed subjects.

Chemical Properties of Dimethylformamide:
N,N-Dimethylformamide is a colorless or slightly yellow liquid with a boiling point of 153°C and a vapor pressure of 380 Pa at 20°C.
Dimethylformamide is freely soluble in water and soluble in alcohols, acetone and benzene.
N,N-Dimethylformamide is used as solvent, catalyst and gas absorbent.
React violently with concentrated sulfuric acid, fuming nitric acid and can even explode.
Pure Dimethylformamide is odorless, but industrial grade or modified Dimethylformamide has a fishy smell because Dimethylformamide contains impurities of Dimethylamine.
Dimethylformamide is unstable (especially at high temperatures) in the presence of a strong base such as sodium hydroxide or a strong acid such as hydrochloric acid or sulfuric acid, and is hydrolyzed to formic acid and dimethylamine.

Molar mass: 73.095 g·mol−1
Appearance: Colourless liquid
Odor: fishy, ammoniacal
Density: 0.948 g/mL
Melting point: −78 °C (−108 °F; 195 K)
Boiling point: 153 °C (307 °F; 426 K)
Solubility in water: Miscible
log P: −0.829
Vapor pressure: 516 Pa
Acidity (pKa): -0.3 (for the conjugate acid) (H2O)
UV-vis (λmax): 270 nm
Absorbance: 1.00
Refractive index (nD): 1.4305 (at 20 °C)
Viscosity: 0.92 mPa s (at 20 °C)

General description
N,N-Dimethylformamide (DMF) is the commonly employed solvent for chemical reactions.
DMF is a useful solvent employed for the isolation of chlorophyll from plant tissues.
Dimethylformamide is widely employed reagent in organic synthesis.
Dimethylformamide plays multiple roles in various reactions such as solvent, dehydrating agent, reducing agent as well as catalyst.
Dimethylformamide is a multipurpose building block for the synthesis of compounds containing O, -CO, -NMe2, -CONMe2, -Me, -CHO as functional groups.
N,N-Dimethylformamide is a polar solvent commonly used in organic synthesis.
Dimethylformamide also acts as a multipurpose precursor for formylation, amination, aminocarbonylation, amidation and cyanation reactions.

Applications of Dimethylformamide:
N,N-Dimethylformamide (anhydrous) has been used as solvent for the synthesis of cytotoxic luteinizing hormone-releasing hormone (LH-RH) conjugate AN-152 (a chemotherapeutic drug) and fluorophore C625 [4-(N,N-diphenylamino)-4′-(6-O-hemiglutarate)hexylsulfinyl stilbene].
Dimethylformamide may be employed as solvent medium for the various organic reduction reactions.

DMF has been used as a solvent in the following processes:
Multi-step synthesis of L-azidohomoalanine (L-Aha) during the substitution of the mesylate by sodium azide.
Synthesis of phosphine-FLAG®, a detection reagent for metabolic labeling of glycans.
Synthesis of per-O-acetylated 6-azidofucose, a per-O-acetylated azido sugar.
Solvent for many hydrophobic organic compounds.

Dimethylformamide (DMF) is a colorless, water-soluble liquid with a faint ammonia-like odor.
Dimethylformamide is used in acrylic fiber spinning, chemical manufacturing, and pharmaceutical production; Dimethylformamide is also present in textile dyes and pigments, paint stripping solvents, and coating, printing, and adhesive formulations.
The National Institute for Occupational Safety and Health (NIOSH) estimates that more than 100,000 workers may be exposed to DMF in the United States.
Currently, there is only one producer of DMF in the United States; annual production is between 50 and 60 million pounds.

Physical properties of Dimethylformamide:
Clear, colorless to light yellow, hygroscopic, mobile liquid with a faint, characteristic, ammonialike odor.
An experimentally determined odor threshold concentration of 100 ppmv was reported by Leonardos et al.

Uses of Dimethylformamide:
N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents.
Dimethylformamide is primarily used as an industrial solvent.
Dimethylformamide solutions are used toprocess polymer fibers, films, and surface coatings; to permit easy spinning of acrylic fibers; to produce wire enamels, and as a crystallization medium in the pharmaceutical industry.
DMF can also be used for formylation with alkyllithium or Grignard reagents.
Dimethylformamide is used as a reagent in Bouveault aldehyde synthesis and also in Vilsmeier-Haack reaction.
Dimethylformamide acts as a catalyst in the synthesis of acyl chlorides.

Dimethylformamide is used for separating and refining crude from olefin gas.
DMF along with methylene chloride acts as a remover of varnish or lacquers.
Dimethylformamide is also used in the manufacture of adhesives, fibers and films.
N,N-Dimethylformamide (DMF) is a solvent with a low evaporation rate, useful for preparing solutions with a variety of hydrophobic organic compounds used in molecular biology applications.
N,N-Dimethylformamide was used to solubilize MTT crystals in cell viability assays.
Dimethylformamide was also used in feruloyl esterase activity assay in molds exhibiting high activity of the enzyme.
The world-wide consumption of DMF in 2001 was approximately 285, 000 metric tonnes and most of that was used as an industrial solvent.

Definition of Dimethylformamide:
ChEBI: A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.

Production Methods of Dimethylformamide:
Industrial production of N,N-Dimethylformamide (DMF) is via three separate processes.
Dimethylamine in methanol is reacted with carbon monoxide in the presence of sodium methoxide or metal carbonyls at 110-150°C and high pressure.
Alternately, methyl formate is produced from carbon monoxide and methanol under high pressure at 60-100°C in the presence of sodium methoxide.
The resulting methyl formate is distilled and then reacted with dimethylamine at 80-100°C and low pressure.
The third process involves reaction of carbon dioxide, hydrogen and dimethylamine in the presence of halogen-containing transition metal compounds to yield DMF.

Preparation of Dimethylformamide:
Two processes are used commercially to produce dimethylformamide.
In the direct or one-step process, dimethylamine and carbon monoxide react at 100°C and 200 psia in the presence of a sodium methoxide catalyst to make dimethylformamide.
The homogenous catalyst is separated from the crude DMF, which is then refined to the final product.
In the indirect process, methyl formate is isolated, and then reacted with dimethylamine to form DMF.
To obtain methyl formate, two methods may be used - dehydrogenation of methanol and esterification of formic acid.

General Description of :
A water-white liquid with a faint fishy odor.
Flash point 136°F.
Slightly less dense than water.
Vapors heavier than air.
May irritate eyes.

Air & Water Reactions
Flammable.
Water soluble.

Reactivity Profile
N,N-Dimethylformamide may react violently with a broad range of chemicals, e.g.: alkaline metals (sodium, potassium), azides, hydrides (sodium borohydride, lithium aluminum hydride), bromine, chlorine, carbon tetrachloride, hexachlorocyclohexane, phosphorus pentaoxide, triethylaluminum, magnesium nitrate, organic nitrates.
Forms explosive mixtures with lithium azide.
Oxidation by chromium trioxide or potassium permanganate may lead to explosion.

Quality Level: 300
grade: anhydrous
vapor density: 2.5 (vs air)
vapor pressure: 2.7 mmHg ( 20 °C)
assay: 99.8%
form: liquid
autoignition temp.: 833 °F
expl. lim.: 15.2 %
impurities: <0.005% water
evapn. residue: <0.0005%
refractive index: n20/D 1.430 (lit.)
pH: 7 (20 °C, 200 g/L)
bp: 153 °C (lit.)
mp: −61 °C (lit.)
density: 0.944 g/mL (lit.)
SMILES string: [H]C(=O)N(C)C
InChI: 1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
InChI key: ZMXDDKWLCZADIW-UHFFFAOYSA-N

Dimethylformamide (DMF) is a clear, colorless, hygroscopic liquid with a slight amine odor.
The solvent properties of DMF are particularly attractive because of the high dielectric constant, the aprotic nature of the solvent, Dimethylformamides wide liquid range and low volatility.
Dimethylformamide is frequently used for chemical reactions and other applications, which require a high solvency power.
The product is known as a universal solvent.
The high solubility of polyacrylonitrile in DMF, together with the good miscibility of DMF in water makes DMF the preferred solvent for the production of acrylic fibers.
Also the spinning of polyurethane based elastomers is performed from DMF based solutions.

Another significant application is the use of DMF as a solvent for polyurethane-based coatings on leather and artificial leather fabrics.
Polymers like polyvinylchloride, vinylchloride- vinylacetate copolymers and some polyamides are also readily dissolved in DMF.
DMF is also used in epoxy based formulations.
The pharmaceutical industry uses DMF as a reaction and crystallization solvent because of its exceptional solvency parameters.
In the petrochemical industry DMF is used for the purification of acetylene from ethylene and butadiene from C4 streams.
Also for the separation of aromatics, which can be easily dissolved by DMF from aliphatic hydrocarbons.
Those aliphatics are used in lube oils.

Due to the high solubility of SO2 in DMF, exhaust combustion streams from high sulfur containing fuels can be purified with CO2 being recovered.
Inorganic and organic based residual fluxes are highly soluble in DMF; therefore this solvent is used as a cleaner, for instance to clean hot-dip tinned parts.
DMF is also used as industrial paint stripper.
This high solubility of inorganic substances also leads to the application of DMF in the production of high voltage capacitors.
DMF is also used as carrier for inks and dyes in various printing and fiber-dying applications.
DMF is widely used as a solvent, reagent and catalyst in the synthetic organic chemistry.

Applications/uses of Dimethylformamide:
-Agricultural chemical processing
-Fibers
-HTF - pharmaceutical processing
-Oil or gas processing
-Polymer processing
-Process solvents
-Refining
-Textile

This procedure is adequate for most laboratory purposes.
Larger amounts of water can be removed by azeotropic distillation with *benzene (10% v/v, previously dried over CaH2), at atmospheric pressure: water and *benzene distil below 80o.
The liquid remaining in the distillation flask is further dried by adding MgSO4 (previously ignited overnight at 300-400o) to give 25g/L.
After shaking for one day, a further quantity of MgSO4 is added, and the DMF is distillied at 15-20mm pressure through a 3-ft vacuum-jacketed column packed with steel helices.

However, MgSO4 is an inefficient drying agent, leaving about 0.01M water in the final DMF.
More efficient drying (to around 0.001-0.007M water) is achieved by standing with powdered BaO, followed by decanting before distillation, then with alumina powder (50g/L, previously heated overnight to 500-600o), and distilling from more of the alumina, or by refluxing at 120-140o for 24hours with triphenylchlorosilane (5-10g/L), then distilling at ca 5mm pressure.
Free amine in DMF can be detected by the colour reaction with 1-fluoro-2,4-dinitrobenzene.
Dimethylformamide has also been purified by drying overnight over KOH pellets and then distilling from BaO through a 10 cm Vigreux column (p 11).
Dimethylformamide has been purified by distilling from K2CO3 under high vacuum and fractionated in an all-glass apparatus.

Chemical Synthesis of Dimethylformamide:
N,N-Dimethylformamide is predominantly produced in a single-step reaction between dimethylamine and carbon monoxide under pressure at high temperatures and in the presence of basic catalysts such as sodium methoxide.
The crude product contains methanol and N,N-dimethylformamide with increased purity (up to 99.9%) is obtained by multiple distillations.
Alternatively, Dimethylformamide can be produced by a two-step process in which methyl formate is prepared separately and, in a second step, reacts with dimethylamine under similar conditions as those described for the single-step reaction.
No catalysts are involved in the process.

Dimethylformamide (DMF) is a colourless liquid with only a slight, unpleasant odour; smell is, therefore, not a useful warning signal.
DMF is usually stable but, when Dimethylformamide comes into contact with strong oxidizers, halogens, alkylaluminium, or halogenated hydrocarbons (especially in combination with metals), Dimethylformamide may cause fires and explosions.
DMF is completely miscible with water and most organic solvents.
Dimethylformamide has a relatively low vapour pressure.

As a solvent, or a chemical that mixes with other liquids, dimethylformamide is used in the formation of many products that require a strong chemical reaction.
Dimethylformamides high boiling point leaves Dimethylformamide with low evaporation potential, so Dimethylformamide will not quickly dissipate when used with other chemicals at high temperatures.
Many plastics and curing processes, such as the curing done to leather, need this chemical to complete the product or process.
Dimethylformamide also can be used to break down many organic compounds.

Dimethylformamide is a neutral compound, so Dimethylformamide does not react very well when paired with a strong acid or base.
A strong base would be a compound such as sodium hydroxide, and a strong acid would be something such as sulfuric acid.
When a base or acid is paired with this compound, Dimethylformamide will revert to Dimethylformamides two original components.
This reverting process is increased if placed in a high-temperature vat.

Dimethylformamide (DMF) is an organic compound that is used as a solvent for many products, including lacquers, pigments and dyes.
Known as a volatile organic compound (VOC), DMF can endanger both humans and wildlife, but the threat is regarded as minimal because Dimethylformamide does not occur in nature and isn't encountered by humans outside of occupational settings.
Dimethylformamide is not stable when strong acids or bases are around Dimethylformamide, and Dimethylformamide hydrolyzes back into Dimethylformamides original state of dimethylamine and formic acid.
According to the Material Safety Data Sheet (MSDS), dimethylformamide is hazardous to health, flammable, reacts to skin on contact and poses a minimal threat of reacting with other chemicals.

Dimethylformamide
Dimethylformamide (DMF) is a colorless liquid that is miscible with both water and many organic liquids.
Dimethylformamide has been called the “universal solvent” and has been used as such in many commercial applications.
Production of DMF was estimated at 125,000 tons.84 In addition to Dimethylformamides synthesis, occupational exposure to DMF may occur in the production or use of many resins, inks, and adhesives, as well as in the leather and aircraft repair industries.
Data from NOES indicate that as many as 125,000 U.S. workers were exposed between 1980 and 1983.

Acute, high-level exposure to DMF causes hepatotoxicity as its major effect.
Occupational exposure typically occurs through the dermal or inhalational route.
A high prevalence of abnormal liver enzyme levels has been reported in workers exposed to DMF.
More recently, an outbreak of acute hepatitis occurred in five industrial waste disposal workers exposed to DMF and resulted in one death.
Other associated symptoms included dizziness, anorexia, nausea, and abdominal pain.

An unusual disulfiram-like alcohol intolerance has been noted on multiple occasions in exposed workers.
Liver biopsy specimens from exposed workers revealed focal hepatocellular necrosis and microvesicular steatosis with prominence of smooth endoplasmic reticulum, complex lysosomes, and pleomorphic mitochondria with crystalline inclusions.
Fibrosis was not seen on biopsy of workers with long-term exposure.
Hepatitis B, elevated body mass index, and alcohol use appear to have synergistic effects on DMF hepatotoxicity.
Hepatic necrosis has been documented in multiple animal models with high-level acute exposure.

Dimethylformamide (DMF) is a widely used solvent used in the synthetic resin and leather industries that causes dose-related massive necrosis in animals and is capable of producing focal hepatic necrosis and microvesicular steatosis in humans, the severity of which correlates with the duration of occupational exposure.
Most individuals with prolonged DMF exposure (>1 year) had symptomatic disease that slowly resolved when they were removed from the workplace.
Re-exposure in one individual produced recurrent injury.
In a series of workers from Italy, 23% had LFT abnormalities, and 50% reported disulfiram-like symptoms.
Workers in a Chinese organic chemical factory who were exposed to DMF had levels of DMF metabolites in their urine that correlated with LAE elevations.

Hydrazine and Dimethylformamides derivatives are experimental hepatotoxins and carcinogens.
Steatosis and focal necrosis have been reported in humans.
Bromoalkanes and iodoalkanes have been used in insecticides and aircraft fuels, with rare reports of hepatic injury.
Ethylene dibromide (dibromoethane) produces zone 3 necrosis in experimental animals, with at least one case of necrosis after an attempted-suicide ingestion.
Occupational exposure has been linked to fatal toxicity, which may be potentiated by the concomitant use of disulfiram.

N,N-Dimethylformamide (DMF) is frequently used as a solvent because of its unique physical properties that allow Dimethylformamide to solubilize both organic and inorganic substances.
Dimethylformamide has also found broad applications as a catalyst for a variety of chemical transformations and as a donor for many functional groups in synthetic organic chemistry.
However, DMF is incompatible with a wide variety of substances and has resulted in many incidents over the years.
Analysis of literature information indicates that those incompatible substances can be categorized as acids, bases, halogenated reagents, oxidants, and reductants.
This comprehensive review of the potential hazards of using DMF in chemical reactions will serve as an educational resource to promote awareness of such safety hazards in the broader chemistry community and encourage scientists to develop appropriate control strategies to mitigate the potential safety risks associated with the use of DMF in chemical reactions.

DMF is a clear liquid with high boiling point.
DMF is considered to be biodegradable, but is toxic by inhalation or skin adsorption.
DMF is produced by reaction of dimethylamine and carbon monoxide (single step process).

Beilstein/REAXYS Number: 605365
MDL number: MFCD00003284
PubChem Substance ID: 57647999
NACRES: NA.21

N,N-Dimethylformamide (DMF) is frequently used as an aprotic solvent in chemical transformations in laboratories of academia as well as in those of chemical industry.
In the present review, we will reveal that DMF is actually something much more than a solvent.
Dimethylformamide is a unique chemical since, as well as being an effective polar aprotic solvent, Dimethylformamide can play three other important roles in organic chemistry.
Dimethylformamide can be used as a reagent, a catalyst, and a stabilizer.

Melting point:-61 °C (lit.)
alpha 0.94 º
Boiling point:153 °C (lit.)
Density 0.944 g/mL (lit.)
vapor density 2.5 (vs air)
vapor pressure 2.7 mm Hg ( 20 °C)
refractive index n20/D 1.430(lit.)
Flash point:136 °F
storage temp. Store at +5°C to +30°C.
solubility water: miscible
pka-0.44±0.70(Predicted)
form Powder
color APHA: ≤15
PH7 (200g/l, H2O, 20℃)
OdorFaint, ammonia-like odor detectable at 100 ppm
Relative polarity0.386
Odor Threshold1.8ppm
explosive limit2.2-16%(V)
Water Solubility soluble
λmaxλ: 270 nm Amax: 1.00
λ: 275 nm Amax: 0.30
λ: 295 nm Amax: 0.10
λ: 310 nm Amax: 0.05
λ: 340-400 nm Amax: 0.01
Sensitive Hygroscopic
Merck 14,3243
BRN 605365

Exposure limits: NIOSH REL: TWA 10 ppm (30 mg/m3), IDLH 500 ppm; OSHA PEL: TWA 10 ppm; ACGIH TLV: TWA 10 ppm (adopted).
InChIKeyZMXDDKWLCZADIW-UHFFFAOYSA-N
Indirect Additives used in Food Contact SubstancesN,N-DIMETHYLFORMAMIDE
FDA 21 CFR175.105; 176.300
CAS DataBase Reference68-12-2(CAS DataBase Reference)
EWG's Food Scores4-7
FDA UNII8696NH0Y2X
NCI Dictionary of Cancer TermsEMF
NIST Chemistry ReferenceFormamide, N,N-dimethyl-(68-12-2)
Proposition 65 ListN,N-Dimethylformamide
IARC2A (Vol. 47, 71, 115) 2018
EPA Substance Registry SystemN,N-Dimethylformamide (68-12-2)

Chemical name / synonym: N-N-Dimethylformamide
Formula: (CH3) 2NOCH
Appearance: colorless liquid
Title:> = 99%
Density: 0.95 kg / l at 20 ° C
Boiling point: 153 ° C
Flash point: 58 ° C

Metabolic pathway
Three urinary metabolites are identified in humans and rodents, and the metabolites quantified are N- (hydroxymethyl)-N-methylformamide (HMMF), resulting in N-methylformamide (NMF) and N-acetyl-S-(N- methylcarbamoyl)cysteine (AMCC).
Ten volunteers who absorb between 28 and 60 mmol/kg DMF during an 8 h exposure to DMF in air at 6 mg=m3 excrete in the urine within 72 h between 16.1 and 48.7% of the dose as HMMF, between 8.3 and 23.9% as formamide, and between 9.7 and 22.8% as AMCC.
AMCC together with HMMF is also detected in the urine of workers after occupational exposure to DMF.
There is a quantitative difference between the metabolic pathway of DMF to AMCC in humans and rodents.

storage of Dimethylformamide:
DMF should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

Purification Methods
DMF decomposes slightly at Dimethylformamides normal boiling point to give small amounts of dimethylamine and carbon monoxide.
The decomposition is catalysed by acidic or basic materials, so that even at room temperature DMF is appreciably decomposed if allowed to stand for several hours with solid KOH, NaOH or CaH2.
If these reagents are used as dehydrating agents, therefore, they should not be refluxed with the DMF.
Use of CaSO4, MgSO4, silica gel or Linde type 4A molecular sieves is preferable, followed by distillation under reduced pressure.

The middle fraction is collected, degassed (seven or eight freeze-thaw cycles) and redistilled under as high a vacuum as possible.
Rapid purification: Stir over CaH2 (5% w/v) overnight, filter, then distil at 20mmHg.
Store the distilled DMF over 3A or 4A molecular sieves.
For solid phase synthesis, the DMF used must be of high quality and free from amines.

Incompatibilities
Though stable at normal temperatures and storage conditions, DMF may react violently with halogens, acyl halides, strong oxidizers, and polyhalogenated compounds in the presence of iron.
Decomposition products include toxic gases and vapors such as dimethylamine and carbon monoxide.
DMF will attack some forms of plastics, rubber, and coatings.

Waste Disposal
Excess DMF and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

Physical Properties
Colorless, clear liquid
bp 153 °C, mp -61 °C
Miscible with water in all proportions

Odor: Faint, ammonia-like odor detectable at 100 ppm
Vapor Density: 2.5 (air = 1.0)
Vapor Pressure: 2.6 mmHg at 20 °C
Flash Point: 58 °C
Autoignition Temperature: 445 °C

Properties of Dimethylformamide:
Chemical properties of:
DMF penetrates most types of plastic and causes them to swell.

Physical properties of Dimethylformamide:
Dimethylformamide is an odorless, colorless liquid, miscible with water and most organic liquids.
Technical grade or degraded samples often have a fishy smell due to impurities, such as dimethylamine, though obtaining completely 100% odorless DMF is extremely difficult due to dimethylamine's strong odor and is not always done.

Chemical Formula: (CH3)2NCHO
Molecular Weight: 73.0953
Appearance: Colorless liquid
Odor: Slight amine smell
Specific Gravity (liquid 25℃/4℃): 0.9445
Boiling Point (℃ 760mmHg): 153
Freezing Point (℃ 760mmHg): -61
Flash Point (℃ Tagliabue (Tag) Closed Cup): 60
Ignition Temperature (℃): 445
Flammability Limits (vol%): 2.2-15.2
Vapour Pressure (mmHg 25℃): 3.7
Viscosity (CP 25℃): 0.796
Solubility: Readily soluble in water, ether, Ketoalchohol
Stability&Reactivity: Decompose into carbon monoxide when heated

Product Name : N,N-Dimethylformamide
Catalog Codes : SLD4261, SLD3331
CAS# : 68-12-2
RTECS : LQ2100000
TSCA : TSCA 8(b)
Inventory : N,N-Dimethylformamide
Synonym : DMF; Dimethyl Formamide
Chemical Name : N,N-Dimethylformamide

Structure and properties
Due to the contribution of the two possible resonance structures of an amide, the bond order of the carbonyl C=O bond is reduced, while that of the carbon-nitrogen bond is increased.
Thus the infrared spectrum of DMF shows a lower C=O stretching frequency at 1675 cm-1 than an unsubstuted C=O bond.
Also, because of the partial double bond character, the rotation about the C-N axis is slow, making the two methyl groups inequivalent on the NMR time scale, giving rise to two singlets of 3 protons each at δ 2.97 and 2.88, instead of one singlet of 6 protons in the proton NMR spectrum.

Applications
The primary use of dimethylformamide is as a solvent with low evaporation rate.
Dimethylformamide is used in the production of acrylic fibers and plastics.
Dimethylformamide is also used as a solvent in peptide coupling for pharmaceuticals, in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.

Dimethylformamide is used as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction, another useful method of forming aldehydes.
DMF penetrates most plastics and makes them swell.
Dimethylformamide therefore frequently occurs as a component of paint strippers.
Dimethylformamide is also used in the manufacturing of solvent dyes as an important raw material.
Dimethylformamide is consumed during reaction.

Production
Dimethyl formamide is produced with catalyzed reaction of dimethyl amine and carbon monoxide at low pressure and temperature.
Dimethylformamide may also be prepared on a laboratory scale by reacting dimethylamine with formic acid.

Precautions
Reaction with sodium hydride in DMF as a solvent are somewhat hazardous; exothermic decomposition has been reported at temperatures as low as 26 °C.
On a laboratory scale any thermal runaway is (usually) quickly noticed and brought under control with an ice bath and this remains a popular combination of reagents.
On a pilot plant scale, on the other hand, several accidents have been reported.

DMF is a colorless, fishy smelling liquid which is miscible with water and many other organic solvents.
Dimethylformamide is a solvent commonly used in the production of polyurethane coated materials such as synthetic leathers.
Dimethylformamide can also be used to process coatings, adhesives, plastics, acrylic fibers, PU resins, or as a cleaning solvent.

The liquid structure of the commonly used solvents dimethylformamide (DMF) and dimethylacetamide (DMA)were measured using state-of-the-art state neutron diffraction augmented with isotopic substitution (NDIS) and interpreted with empirical potential structure refinement (EPSR).
Both solvents are found to develop rich local ordering with similar local packing densities, though with differences related to their three-dimensional molecular structure.
While DMF’s dipole preferentially orientates anti-parallel to maximise hydrogen bonding, DMA favours parallel arrangement maximising non-directional dispersive forces.
The highly-developed local orientational structure found in these solvents rationalises their ability to solvate a range of charged and neutral nanomaterials and highlights that the understanding of nanomaterial dispersions is a multi-body problem in which the geometry of the molecule, as well its dipole moment, must be incorporated.

Dimethylformamide Formula
Dimethylformamide, also known as N,N-Dimethylmethanamide, is an organic solvent used in the chemical industry to manufacture fibers, films and coatings.

Formula and structure: The dimethylformamide chemical formula is C3H7NO and Dimethylformamides molar mass is 73.10 g mol-1.
The extended formula is CHON(CH3)2 and the molecule is formed by an amide group O=CH-N-R and the nitrogen has two methyl groups bond.
The molecular is planar, because even when the nitrogen does not have a double bond (which needs a planar sp2 hybridization); there are some resonance structures that show the nitrogen needs a sp2 conformation.
Dimethylformamides chemical structure can be written as below, in the common representations used for organic molecules.

Dimethylformamide is the organic compound with the formula (CH3)2NC(O)H.
Commonly abbreviated DMF, this colourless liquid is miscible with water and majority of organic liquids.
DMF is a common solvent for chemical reactions.
Pure dimethylformamide is odorless whereas technical grade or degraded dimethylformamide often has a fishy smell due to impurity of dimethylamine.
Dimethylformamides name is derived from the fact that Dimethylformamide is a derivative of formamide, the amide of formic acid.

Dimethylformamide is a polar (hydrophilic) aprotic solvent with a high boiling point.
Dimethylformamide facilitates reactions that follow polar mechanisms, such as SN2 reactions.
Dimethylformamide can be synthesized from formic acid and dimethylamine.
Dimethylformamide is not stable in the presence of strong bases like sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid and is hydrolyzed back into formic acid and dimethylamine, especially at elevated temperatures.

DMF (dimethylformamide) is a recommended solvent for labeling reactions using NHS esters.
However, when DMF is stored in air, Dimethylformamide deteriorates slowly absorbing moisture, and releasing dimethylamine.
These impurities rapidly destroy NHS ester function, decrease labeling efficiency, and even make labeling reaction fail.
Dimethylformamide solvent requires special drying and preparation, which is often not available in all laboratories.
This product contains ready-to use solvent which is guaranteed to be useable for the labeling.
Tubes with high quality, dry, and amine-free DMF are packed under argon.

Dimethylformamide is a colorless organic solvent that is used in the synthesis of organic compounds and acts as a catalyst in carboxylation reactions.
Dimethylformamide is a low to moderate hazard material and the risk of adverse health effects associated with both occupational and consumer use of this chemical is anticipated to be low to moderate.
Dimethylformamide is used in industrial settings only and will not be present within consumer products.
When handled responsibly within industrial settings, the potential for exposure and subsequent risk can be minimized, allowing dimethylformamide to be used safely.

Occurrence: The natural occurrence of dimethylformamide (DMF) has not been reported.

Preparation: The synthesis of dimethylformamide is performed using N,N-methylamine and a solution of sodium methoxide; them a stream of gas carbon monoxide is passed through the solution at 50-150 ºC.
Methanol is used as catalyst of the reaction.

Physical properties: Dimethylformamide is a clear to colorless liquid with a fishy ammoniacal.
Dimethylformamides density is 0.948 g mL-1.
The melting point is -60.5 ºC, and the boiling point is 152-154 ºC.
Dimethylformamide is miscible in water and most of the organic solvents.

Chemical properties: Dimethylformamide is an excellent solvent.
Dimethylformamide can be hydrolyzed by strong acids and bases to form a carboxylic acid and an amine.
DMF can also react through a decarbonylation to produce dymethylamine.
Dimethylformamide reacts with several chemical compounds such as: alkaline metals, azides, hydrides, bromine, chlorine, magnesium nitrate, etc.
Dimethylformamide also can catalyze thesynthesis of acyl halides.

Uses: Dimethyl formamide is used mostly in the manufacture of fibers, plastics, coatings and acrylic products and some adhesives, rubbers and films.
Dimethyl formamide is a solvent used to prepared several medicaments by the pharmaceutical industry.
Moreover, some oils processes use the DMF to recover olefins.
In laboratories, Dimethylformamide is used as solvent to analysis of NMR spectroscopy.

The demand for Dimethylformamide (DMF) has been growing from the chemical industry owing to Dimethylformamides increasing uses as a solvent, a chemical intermediate, and an additive.
DMF is a commonly used solvent in polyurethane coatings, synthetic leathers, and artificial leather fabrics because Dimethylformamide is highly soluble in nature, low volatility and has a low evaporation rate.
Dimethylformamide also used as a solvent for many purposes such as residue in synthetic leather, processing solvents, plastic, rubber, adhesives, and printing inks.
DMF has extraordinary solvency parameters so that Dimethylformamide can be used as a reaction and crystallization solvent for pharmaceutical purposes and DMF is also for purification purposes in pharmaceutical industry.
Increasing uses of solvents and intermediates, expanding textile industries, increasing medical technology, and chemical processing sectors in developing countries are driving the demand for dimethylformamide used for various chemical manufacturing purposes, through the years to come.

Other names
DMF
Dimethylformamide
N,N-Dimethylmethanamide
N,N-DIMETHYLFORMAMIDE (CARBONYL-13C1)
N,N-Dimethylformamide, Spectrophotometric Grade
D0722
D0939
FT-0629532
FT-0629533
FT-0639029
FT-0696040
N,N-Dimethylformamide, for HPLC, >=99.5%
C03134
N,N-DIMETHYLFORMAMIDE
Dimethylformamide
68-12-2
N,N-Dimethylmethanamide
Dimethyl formamide
N-Formyldimethylamine
Formamide, N,N-dimethyl-
Dimethylformamid
DMF
Dimetilformamide
Dwumetyloformamid
DMFA
Formyldimethylamine
N,N-Dimethyl formamide
Dimethylforamide
Dimetylformamidu
DMF (amide)NCI-C60913
dimethyl-Formamide
n,n,dimethylformamide
N,N-Dimethylformamid
Dimethylamid kyseliny mravenci
MFCD00003284
U-4224
UNII-8696NH0Y2X
n,n-dimethyl-Formamide
N, N-dimethylformamide
N,N- Dimethylformamide
N,N-Dimethylformaldehyde
DTXSID6020515
CHEBI:17741
NSC5356
8696NH0Y2X
NSC-5356
Formic acid, amide, N,N-dimethyl-
EINECS 200-679-5
UN2265
N,N-Dimethylformamide, 99.8%, for peptide synthesis
N,N-Dimethylformamide, 99.8+%, for spectroscopy ACS
Dimethylamid kyseliny mravenci [Czech]
EPA Pesticide Chemical Code 366200
N,N-Dimethylformamide, 99.8%, Extra Dry, AcroSeal(R)dimethlforamide
dimethlformamide
dimethyformamide
dimetylformamide
N,N-Dimethylformamide, 99.9%, for biochemistry, AcroSeal(R)
dimehtylformamide
dimethlyformamide
dimethyiformamide
AI3-03311
dimethy formamide
dimethy1formamide
dimethyl foramide
dimethyl formamid
dimehtylformarnide
dimethylformarnide
dimethylforrnamide
dirnethylformamide
N,N-Dimethylformamide, 99.8%, Extra Dry over Molecular Sieve, AcroSeal(R)
di-methylformamide
dimethylf ormamide
dimethylform amide
dimethylform-amide
dimethylformamid e
dimethylformamide-
dirnethylformarnide
N,N-Dimethylformamide, 99.8%, for molecular biology, DNAse, RNAse and Protease free
n-dimethylformamide
dimethyl form-amide
dimethyl- formamide
dimethylfor- mamide
DMF,SP Grade
N,n-dimethylforamide
formamide, dimethyl-
N,N-dimethlformamide
N,N-dimethyformamide
N,N-dimetylformamide
n,n.dimethylformamide
N,N'dimethylformamide
N,N-dimethvlformamide
N.N-dimethylformamide
HCONMe2
Formamide,N-dimethyl-
N, N-dimethylforamide
N,N'-dimethylforamide
N,N-dimethl formamide
N,N-dimethy formamide
N,N-dimethyl foramide
N,N-dimethyl formamid
N,N-dimethylformarnide
N,N-dimethylforrnamide
N,N-dimetyl formamide
N,N-dirnethylformamide
n,n,-dimethylformamide
Dimethylformamide, DMF
DMF, Dimethylformamide
N, N dimethylformamide
N,N -dimethylformamide
N,N dimethyl formamide
N,N' dimethylformamide
N,N-di methylformamide
N,N-di-methylformamide
N,N-dime-thylformamide
N,N-dimehtyl formamide
N,N-dimethylfor mamide
N,N-dimethylfor-mamide
N,N-dimethylform-amide
N,N-dimethylformamide-
PubChem23341
N,N-di-methylforrnamide
Dimethyl Fornamide,(S)
DMF (dimethylformamide)
n,n,-dimethyl formamide
N, N'-dimethylformamide
N, N- dimethylformamide
N, N-di-methylformamide
N, N-dimethyl-formamide
N,N- dimethyl formamide
N,N-di-methyl formamide
N,N-di-methyl-formamide
N,N-dimethyl -formamide
N,N-dimethyl- formamide
N, N-dimethylformaldehyde
bmse000709
EC 200-679-5
D.M.F
HCON(CH3)2
Dynasolve 100 (Salt/Mix)
BIDD:ER0600
WLN: VHN1&1
ACMC-20976q
CHEMBL268291
D.M.F.
N,N-Dimethylformamide, 99.8%
N,N-Dimethylformamide, anhydrous
N,N-Dimethylformamide HPLC grade
N,N-Dimethylformamide, ACS grade
ZINC901648
Dimethylformamide Reagent Grade ACS
Tox21_201259
Tox21_300039
ANW-13584
s6192
STL264197
N,N-Dimethylformamide, LR, >=99%
AKOS000121096
FORMIN ACID,AMIDE,N,N-DIMETHYL
DB01844
EBD2222506
MCULE-6290117712
UN 2265
N,N-Dimethylformamide, p.a., 99.8%
N,N-Dimethylformamide, AR, >=99.5%
NCGC00090785-01
NCGC00090785-02
NCGC00090785-03
NCGC00090785-04
NCGC00090785-05
NCGC00254093-01
NCGC00258811-01
K124
Dimethylformamide, n,n- Reagent Grade ACS
N,N-Dimethylformamide, analytical standard
N,N-Dimethylformamide, anhydrous, 99.8%
N,N-Dimethylformamide, 99.5%, for HPLC
DSSTox_CID_515
DSSTox_RID_75636
DSSTox_GSID_20515
N,N Dimethylformamide
Caswell No. 366A
N,N-Dimethylformamide, HPLC Grade
Dimetylformamidu [Czech]
Dimethylformamid [German]
Dimetilformamide [Italian]
Dwumetyloformamid [Polish]
CAS-68-12-2
HSDB 78
N,N-Dimethylformamide, 99+%, extra pure
N,N-Dimetilformamida
CCRIS 1638
N,N-Dimetilformamida [Spanish]
N,N-Dimethylformamide, 99.5%, for analysis
N,N-Dimethylformamide, for HPLC, >=99.9%
N,N-Dimethylformamide, 99.8+%, ACS reagent
N,N-Dimethylformamide, 99.8%, for spectroscopy
N,N-Dimethylformamide, ACS reagent, >=99.8%
N, N-dimethyl formamide
NSC 5356
D0722
D0939
FT-0629532
FT-0629533
FT-0639029
FT-0696040
N,N-Dimethylformamide, for HPLC, >=99.5%
C03134
N,N-Dimethylformamide, AldraSORB(TM), 99.8%
N,N-Dimethylformamide, ReagentPlus(R), >=99%
A836012
N,N-Dimethylformamide, biotech. grade, >=99.9%
Q409298
N,N-Dimethylformamide, p.a., ACS reagent, 99.8%
N,N-Dimethylformamide, SAJ first grade, >=99.0%
N,N-Dimethylformamide [UN2265] [Flammable liquid]
N,N-Dimethylformamide, anhydrous, ZerO2(TM), 99.8%
N,N-Dimethylformamide, for molecular biology, >=99%
N,N-Dimethylformamide, JIS special grade, >=99.5%
N,N-Dimethylformamide, UV HPLC spectroscopic, 99.7%
N,N-Dimethylformamide, ACS spectrophotometric grade, >=99.8%
N,N-Dimethylformamide HPLC, UV-IR min. 99.9%, isocratic grade
N,N-Dimethylformamide, B&J Brand (product of Burdick & Jackson)
N,N-Dimethylformamide, Vetec(TM) reagent grade, anhydrous, >=99.8%
Dimethylformamide, Pharmaceutical Secondary Standard; Certified Reference Material
N,N-Dimethylformamide, 99.8%, Extra Dry, AcroSeal(R), package of 4x25ML bottles
N,N-Dimethylformamide, p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99.8%
N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., >=99.8% (GC)
N,N-Dimethylformamide, suitable for neutral marker for measuring electroosmotic flow (EOF), ~99%