PRODUCTS

N,N-DIMETHYLFORMAMIDE

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

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

Physical Description

N,n-dimethylformamide 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.
May irritate eyes.

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
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

N,N-dimethylformamide 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.
May irritate eyes.

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

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.

N,N-dimethylformamide 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.

N,N-dimethylformamide 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
N,N-dimethylformamide is hydrolyzed by strong acids and bases, especially at elevated temperatures.
With sodium hydroxide, N,N-dimethylformamide converts to formate and dimethylamine.
N,N-dimethylformamide 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, N,N-dimethylformamide was a reagent in the Vilsmeier–Haack reaction, which is used to formylate aromatic compounds.
The process involves initial conversion of N,N-dimethylformamide to a chloroiminium ion, [(CH3)2N=CH(Cl)]+, known as a Vilsmeier reagent, which attacks arenes.

Organolithium compounds and Grignard reagents react with N,N-dimethylformamide to give aldehydes after hydrolysis in a reaction called Bouveault aldehyde synthesis.

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

Production
N,N-dimethylformamide 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.

N,N-dimethylformamide is prepared by combining methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.

Although currently impractical, N,N-dimethylformamide can be prepared from supercritical carbon dioxide using ruthenium-based catalysts.

Applications
The primary use of N,N-dimethylformamide is as a solvent with low evaporation rate.
N,N-dimethylformamide is used in the production of acrylic fibers and plastics.
N,N-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.

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

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

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

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

Uses
N,N-dimethylformamide is primarily used as an industrial solvent.
N,N-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.

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

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, it 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.

N,N-Dimethylformamide is used predominantly as an aprotic solvent in the manufacture of polyacrylonitrile fibres, and trends in its production parallel those of the polyacrylic fibre industry.
N,N-Dimethylformamide is also used in the manufacture of high quality polyurethane and polyamide coatings (e.g. for leather or artificial leather fabrics), which are otherwise difficult to solubilize, and where a solvent with a slow rate of evaporation is needed.
N,N-Dimethylformamide is commonly used as a solvent in the electronics industry, in pesticides, in industrial paint-stripping applications, and as a reaction and crystallizing solvent in the pharmaceutical industry.
N,N-Dimethylformamide has limited use as a selective solvent for the separation of aliphatic hydrocarbons such as the extraction of acetylene or butadiene from hydrocarbon streams.

Stability / Shelf Life

N,N-Dimethylformamide is stable.
N,N-Dimethylformamide is hygroscopic and easily absorbs water form a humid atmosphere and should therefore be kept under dry nitrogen.
High purity N,N-Dimethylformamide, required for acrylic fibers, is best stored in aluminum tanks.
N,N-Dimethylformamide 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-Dimethylformamid
N,N-Dimetilformamida
HSDB 78
CCRIS 1638
DTXSID6020515
U-4224
Dimetylformamidu [Czech]
Dimethylformamid [German]
Dimetilformamide [Italian]
Dwumetyloformamid [Polish]
NSC 5356
NSC-5356
Formic acid, amide, N,N-dimethyl-
EINECS 200-679-5
EPA Pesticide Chemical Code 366200
UNII-8696NH0Y2X
N,N-Dimetilformamida [Spanish]
CHEBI:17741
AI3-03311
n,n-dimethyl-Formamide
N, N-dimethylformamide
NSC5356
N,N'-Dimethylformamide
N,N- Dimethylformamide
8696NH0Y2X
N,N-Dimethylformaldehyde
N, N-dimethyl formamide
Dimethylformamide, N,N-
MFCD00003284
UN2265
n,n-dimethylformamide-1-d
Dimethylamid kyseliny mravenci [Czech]
DTXCID20515
EC 200-679-5
n,n,dimethylformamide
DIMETHYLFORMAMIDE (MART.)
DIMETHYLFORMAMIDE [MART.]
N,N-DIMETHYLFORMAMIDE (IARC)
N,N-DIMETHYLFORMAMIDE [IARC]
CAS-68-12-2
N,N-Dimethylformamide, for HPLC, >=99.9%
N,N-Dimethylformamide, ACS reagent, >=99.8%
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
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-
DMF (CHRIS Code)
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
Dimethylformamide (DMFA)
N, N-dimethylformaldehyde
Dimethylformamide (N,N-)
bmse000709
D0E1KX
Formamida, n, n-dimetil-
D.M.F
Formamide, N, N-dimethyl-
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]
CS-CZ-00065
Dimethylformamide Reagent Grade ACS
N,N-Dimethylformamide, HPLC Grade
Tox21_201259
Tox21_300039
N,N-DIMETHYLFORMAMIDE [HSDB]
N,N-Dimethylformamide, biotech grade
NA2265
s6192
STL264197
N,N-Dimethylformamide, LR, >=99%
AKOS000121096
FORMIN ACID,AMIDE,N,N-DIMETHYL
DB01844
LS-1577
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
N,N-dimethylformamide; dimethyl formamide
Dimethylformamide, n,n- Reagent Grade ACS
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 [UN2265] [Flammable liquid]
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%