PRODUCTS

DIMETHYLFORMAMIDE (DMF)

Dimethylformamide (DMF) is an organic compound with the formula (CH3)2N−C(=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.
Dimethylformamide (DMF) is a common solvent for chemical reactions.
Dimethylformamide (DMF) 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 samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, Dimethylformamide (DMF) is structurally related to formamide, having two methyl groups in the place of the two hydrogens.
Dimethylformamide (DMF) is a polar (hydrophilic) aprotic solvent with a high boiling point.
Dimethylformamide (DMF) facilitates reactions that follow polar mechanisms, such as SN2 reactions.

CAS: 68-12-2
European Community (EC) Number: 200-679-5

IUPAC Name: N,N-dimethylformamide

Molecular Formula: C3H7NO, HCON(CH3)2
Molecular Weight: 73.09 g/mol

Experimental Properties:

Color / Form: Colorless to very slightly yellow liquid
Odor: Fishy odor
Boiling Point: 300 to 313 °F at 760 mmHg
Melting Point: -78 °F
Flash Point: 153 °F
Solubility: greater than or equal to 100 mg/mL at 72 °F
Density: 0.95 at 68 °F
Vapor Density: 2.51
Vapor Pressure: 3.7 mmHg at 77 °F ; 2.7 mmHg at 68 °F
Autoignition Temperature: 833 °F
Viscosity: 0.802 cP at 25 °C
Heat of Vaporization: 47.6 kJ/mole at 25 °C
pH: 6.7 (0.5 molar solution in water)
Surface Tension: 36.42 dyne/cm at 25 °C
Ionization Potential: 9.12 eV

Dimethylformamide (DMF) is a member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.
Dimethylformamide (DMF) has a role as a polar aprotic solvent, a hepatotoxic agent and a geroprotector.
Dimethylformamide (DMF) is a volatile organic compound and a member of formamides.
Dimethylformamide (DMF) is functionally related to a formamide.

Dimethylformamide (DMF) appears as a water-white liquid with a faint fishy odor.
Flash point 136 °F.
Slightly less dense than water.
Vapors heavier than air.
Toxic by inhalation or skin absorption.

Dimethylformamide (DMF) is an organic compound with the formula (CH3)2N−C(=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.
Dimethylformamide (DMF) is a common solvent for chemical reactions.
Dimethylformamide (DMF) 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 samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, Dimethylformamide (DMF) is structurally related to formamide, having two methyl groups in the place of the two hydrogens.
Dimethylformamide (DMF) is a polar (hydrophilic) aprotic solvent with a high boiling point.
It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

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.

Dimethylformamide (DMF) is prepared by combining methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.
Although currently impractical, Dimethylformamide (DMF) can be prepared from supercritical carbon dioxide using ruthenium-based catalysts.

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

Dimethylformamide (IUPAC name N,N-dimethylfomamide) is structurally the same as formamide but with two methyl groups replacing the two hydrogens.
Dimethylformamide (DMF) is a clear and odorless liquid, with widespread use as a solvent.

The primary use of Dimethylformamide (DMF) is as a solvent with low evaporation rate.
Dimethylformamide (DMF) is used in the production of acrylic fibers and plastics.
Dimethylformamide (DMF) 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.

Common Uses and Applications:

- Peptide-coupling in pharmaceuticals
- Pesticide production
- Organic synthesis
- Solid-phase peptide synthesis
- NMR spectroscopy standard
- Adhesives
- Fibers and synthetic leathers
- Industries
- Research Laboratories
- Pharmaceutical Industry
- Textiles Industry

Dimethylformamide (DMF) is a clear, colorless, hygroscopic liquid with a slight amine odor.
The solvent properties of Dimethylformamide (DMF) are particularly attractive because of the high dielectric constant, the aprotic nature of the solvent, its wide liquid range and low volatility.
Dimethylformamide (DMF) is frequently used for chemical reactions and other applications, which require a high solvency power.
Dimethylformamide (DMF) is known as a universal solvent.
The high solubility of polyacrylonitrile in Dimethylformamide (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 Dimethylformamide (DMF) based solutions.

Another significant application is the use of Dimethylformamide (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 Dimethylformamide (DMF).
Dimethylformamide (DMF) is also used in epoxy based formulations.

The pharmaceutical industry uses Dimethylformamide (DMF) as a reaction and crystallization solvent because of its exceptional solvency parameters.

In the petrochemical industry Dimethylformamide (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 Dimethylformamide (DMF) from aliphatic hydrocarbons.
Those aliphatics are used in lube oils.

Due to the high solubility of SO2 in Dimethylformamide (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 Dimethylformamide (DMF); therefore this solvent is used as a cleaner, for instance to clean hot-dip tinned parts.
Dimethylformamide (DMF) is also used as industrial paint stripper.

This high solubility of inorganic substances also leads to the application of Dimethylformamide (DMF) in the production of high voltage capacitors.

Dimethylformamide (DMF) is also used as carrier for inks and dyes in various printing and fiber-dying applications.

Dimethylformamide (DMF) is widely used as a solvent, reagent and catalyst in the synthetic organic chemistry.

DMF (dimethylformamide) is a recommended solvent for labeling reactions using NHS esters.
However, when Dimethylformamide (DMF) is stored in air, it 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.

Dimethylformamide (DMF) contains ready-to use solvent which is guaranteed to be usable for the labeling.
Tubes with high quality, dry, and amine-free DMF are packed under argon.

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

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

Dimethylformamide (DMF) is an organic solvent produced in large quantities throughout the world.
Dimethylformamide (DMF) is used in the chemical industry as a solvent, a chemical intermediate, and an additive.

Dimethylformamide is a colorless, polar and organic compound with the formula C3H7NO, abbreviated as DMF.
Dimethylformamide (DMF) is miscible in all proportions with water and is soluble in the majority of organic liquids.
Consequently, Dimethylformamide (DMF) serves as an excellent universal solvent for a variety of substances in all aggregation states.
Dimethylformamide (DMF) finds its application in the processing of agricultural chemicals, fibers, oil or gas, polymers, process solvents, refining and textiles.
In the industry Dimethylformamide (DMF) is used as intermediate for the manufacturing of other substances and as a catalyst in synthesis reaction.
Furthermore, there is a continuously increasing demand on Dimethylformamide (DMF) from industries manufacturing drugs, acrylic fibers and printed circuit boards (PCB’s) as well.
Based on the application’s requirements different grades of the solvent are used.

Structure and properties

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.

Dimethylformamide (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 Dimethylformamide (DMF) shows only one signal for the methyl groups.

Dimethylformamide (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 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
Dimethylformamide (DMF) is hydrolyzed by strong acids and bases, especially at elevated temperatures.
With sodium hydroxide, Dimethylformamide (DMF) converts to formate and dimethylamine.
Dimethylformamide (DMF) undergoes decarbonylation near its boiling point to give dimethylamine.
Distillation is therefore conducted under reduced pressure at lower temperatures.

In one of its main uses in organic synthesis, Dimethylformamide (DMF) was a reagent in the Vilsmeier–Haack reaction, which is used to formylate aromatic compounds.
The process involves initial conversion of Dimethylformamide (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 called Bouveault aldehyde synthesis.

Dimethylformamide forms 1:1 adducts with a variety of Lewis acids such as the soft acid I2, and the hard acid phenol.
It is classified as a hard Lewis base and its ECW model base parameters are EB= 2.19 and CB= 1.31.
Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.

Applications

- Dimethylformamide (DMF) is used as a reagent in the Bouveault aldehyde synthesis and in the Vilsmeier-Haack reaction, another useful method of forming aldehydes.
- Dimethylformamide (DMF) is a common solvent in the Heck reaction.
- Dimethylformamide (DMF) 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 (also known as the 'Vilsmeier reagent').

- Dimethylformamide (DMF) penetrates most plastics and makes them swell.
Because of this property Dimethylformamide (DMF) is suitable for solid phase peptide synthesis and as a component of paint strippers.
-Dimethylformamide (DMF) is used as a solvent to recover olefins such as 1,3-butadiene via extractive distillation.
- Dimethylformamide (DMF) is also used in the manufacturing of solvent dyes as an important raw material.
Dimethylformamide (DMF) 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 it safe to transport and use.

As a cheap and common reagent, Dimethylformamide (DMF) has many uses in a research laboratory.

- Dimethylformamide (DMF) is effective at separating and suspending carbon nanotubes, and is recommended by the NIST for use in near infrared spectroscopy of such.
- Dimethylformamide (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 (DMF) is used as a source of carbon monoxide ligands.
- Dimethylformamide (DMF) is a common solvent used in electrospinning.
- Dimethylformamide (DMF) is commonly used in the solvothermal synthesis of metal–organic frameworks.
- Dimethylformamide (DMF)-d7 in the presence of a catalytic amount of KOt-Bu under microwave heating is a reagent for deuteration of polyaromatic hydrocarbons.

- Agricultural chemical processing
- Fibers
- HTF - pharmaceutical processing
- Oil or gas processing
- Polymer processing
- Process solvents
- Refining
- Textile

Stability / Shelf Life

Dimethylformamide (DMF) is stable.
Dimethylformamide (DMF) is hygroscopic and easily absorbs water form a humid atmosphere and should therefore be kept under dry nitrogen.
High purity Dimethylformamide (DMF), required for acrylic fibers, is best stored in aluminum tanks.
Dimethylformamide (DMF) dose not change under light or oxygen and does not polymerize spontaneously.
Temperatures >350 °C may cause decomposition to form dimethylamine and carbon dioxide, with pressure developing in closed containers.

SYNONYMS:

N,N-DIMETHYLFORMAMIDE
Dimethylformamide
68-12-2
Dimethyl formamide
N,N-Dimethylmethanamide
N-Formyldimethylamine
Formamide, N,N-dimethyl-
Dimethylformamid
DMF
DMFA
Dimetilformamide
Dwumetyloformamid
Formyldimethylamine
N,N-Dimethyl formamide
Dimetylformamidu
DMF (amide)
Dimethylforamide
NCI-C60913
N,N Dimethylformamide
Dimethylamid kyseliny mravenci
Caswell No. 366A
dimethyl-Formamide
n,n,dimethylformamide
N,N-Dimetilformamida
HSDB 78
CCRIS 1638
DTXSID6020515
U-4224
NSC 5356
NSC-5356
Formic acid, amide, N,N-dimethyl-
EINECS 200-679-5
EPA Pesticide Chemical Code 366200
UNII-8696NH0Y2X
CHEBI:17741
AI3-03311
n,n-dimethyl-Formamide
NSC5356
N,N- Dimethylformamide
8696NH0Y2X
N,N-Dimethylformaldehyde
MFCD00003284
n,n-dimethylformamide-1-d
DTXCID20515
EC 200-679-5
N,N-Dimethylformamid
DIMETHYLFORMAMIDE (MART.)
DIMETHYLFORMAMIDE [MART.]
Dimetylformamidu [Czech]
Dimethylformamid [German]
N,N-DIMETHYLFORMAMIDE (IARC)
N,N-DIMETHYLFORMAMIDE [IARC]
Dimetilformamide [Italian]
Dwumetyloformamid [Polish]
CAS-68-12-2
MFCD00003286
N,N-Dimetilformamida [Spanish]
DMF; Dimethylformamide; N,N-Dimethylformamide
N,N-Dimethylformamide, for HPLC, >=99.9%
N, N-dimethylformamide
N,N-Dimethylformamide, ACS reagent, >=99.8%
N, N-dimethyl formamide
UN2265
Dimethylamid kyseliny mravenci [Czech]
dimethlforamide
dimethlformamide
dimethyformamide
dimetylformamide
dimehtylformamide
dimethlyformamide
dimethyiformamide
dimethy formamide
dimethy1formamide
dimethyl foramide
dimethyl formamid
dimehtylformarnide
dimethylformarnide
dimethylforrnamide
dirnethylformamide
di-methylformamide
dimethylf ormamide
dimethylform amide
dimethylform-amide
dimethylformamid e
dimethylformamide-
dirnethylformarnide
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
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-
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|-Dimethylformamide
N, N-dimethylformaldehyde
bmse000709
D.M.F
HCON(CH3)2
Dynasolve 100 (Salt/Mix)
BIDD:ER0600
WLN: VHN1&1
CHEMBL268291
D.M.F.
N,N-Dimethylformamide, 99.8%
N,N-Dimethylformamide, anhydrous
N,N-Dimethylformamide HPLC grade
N,N-Dimethylformamide, ACS grade
N,N-DIMETHYLFORMAMIDE [MI]
N,N-Dimethylformamide, HPLC Grade
Tox21_201259
Tox21_300039
N,N-DIMETHYLFORMAMIDE [HSDB]
N,N-Dimethylformamide, biotech grade
s6192
N,N-Dimethylformamide, LR, >=99%
AKOS000121096
FORMIN ACID,AMIDE,N,N-DIMETHYL
DB01844
N,N-DIMETHYLFORMAMIDE [USP-RS]
N,N-DIMETHYLFORMAMIDE [WHO-DD]
UN 2265
N,N-Dimethylformamide, p.a., 99.8%
USEPA/OPP Pesticide Code: 366200
N,N-Dimethylformamide, AR, >=99.5%
NCGC00090785-01
NCGC00090785-02
NCGC00090785-03
NCGC00090785-04
NCGC00090785-05
NCGC00254093-01
NCGC00258811-01
SY010600
N,N-Dimethylformamide, analytical standard
N,N-Dimethylformamide, anhydrous, 99.8%
D0722
D0939
FT-0629532
FT-0629533
FT-0639029
FT-0696040
N,N-Dimethylformamide, anhydrous, amine free
N,N-Dimethylformamide, for HPLC, >=99.5%
C03134
N,N-Dimethylformamide, Spectrophotometric Grade
N,N-Dimethylformamide, AldraSORB(TM), 99.8%
N,N-Dimethylformamide, ReagentPlus(R), >=99%
A836012
N,N-Dimethylformamide, biotech. grade, >=99.9%
Q409298
InChI=1/C3H7NO/c1-4(2)3-5/h3H,1-2H
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%
Z220615596
N,N-Dimethylformamide, ACS spectrophotometric grade, >=99.8%
N,N-Dimethylformamide HPLC, UV-IR min. 99.9%, isocratic grade
N,N-Dimethylformamide, Vetec(TM) reagent grade, anhydrous, >=99.8%
Dimethylformamide, Pharmaceutical Secondary Standard; Certified Reference Material
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%