Irritation of eyes, skin and nose. May cause nausea.
This is an organic solvent for vinyl resins and acetylene, butadiene, and acid gases. It caused contact dermatitis in a technician at an epoxy resin factory and can provoke alcohol-induced flushing in exposed subjects.
Solvent for liqs and gases. In the synthesis of organic compounds. Solvent for Orlon and similar polyacrylic fibers. Wherever a solvent with a slow rate of evaporation is required. Has been termed the universal organic solvent.
Dimethylformamide is shorted for DMF. It is a compound formed by the substitution of the formic acid's hydroxyl group with dimethylamino group and the molecular formula HCON(CH3)2. It is a clear, transparent, high-boiling point liquid with a light amine flavor and a relative density of 0.9445 (25°C). React violently with concentrated sulfuric acid, fuming nitric acid and can even explode. It is soluble in water and most organic solvents that used as a common solvent for chemical reactions. Pure Dimethylformamide is odorless, but industrial grade or modified Dimethylformamide has a fishy smell because it 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.
The acute LD50 (oral, rats and mice) is 2.2-7.55 mg/kg. Hazards of DMF have been examined.
DMF is stable. It is hygroscopic and easily absorbs water form a humid atmosphere and should therefore be kept under dry nitrogen. High purity DMF, required for acrylic fibers, is best stored in aluminum tanks. DMF does not change under light or oxygen and does not polymerize spontaneously. Temperatures >350 deg C may cause decomposition to form dimethylamine and carbon dioxide, with pressure developing in closed containers.
Clear colorless liquid
Special Hazards of Combustion Products: Vapors are irritating
Solvent for many hydrophobic organic compounds.
DMF decomposes slightly at its 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. 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 [Thomas & Rochow J Am Chem Soc 79 1843 1957]. Free amine in DMF can be detected by the colour reaction with 1-fluoro-2,4-dinitrobenzene. It has also been purified by drying overnight over KOH pellets and then distilling from BaO through a 10 cm Vigreux column (p 11) [Jasiewicz et al. Exp Cell Res 100 213 1976]. [For efficiency of desiccants in drying dimethylformamide see Burfield & Smithers J Org Chem 43 3966 1978, and for a review on purification, tests of purity and physical properties, see Juillard Pure Appl Chem 49 885 1977.] It has been purified by distilling from K2CO3 under high vacuum and fractionated in an all-glass apparatus. The middle fraction is collected, degassed (seven or eight freeze-thaw cycles) and redistilled under as high a vacuum as possible [Mohammad & Kosower J Am Chem Soc 93 2713 1971]. [Beilstein 4 IV 171.] 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.
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.
- It is used as a reagent in Bouveault aldehyde synthesis and also in Vilsmeier-Haack reaction. It acts as a catalyst in the synthesis of acyl chlorides. It is used for separating and refining crude from olefin gas. DMF along with methylene chloride acts as a remover of varnish or lacquers. It 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.It 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.
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.
Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility.
The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace.
Symptoms of acute exposure in humans include abdominal pain, nausea, vomiting, jaundice, alcohol intolerance, and rashes.
Chronic (long-term) occupational exposure to dimethylformamide by inhalation has resulted in effects on the liver and digestive disturbances in workers.
Human Studies have shown a possible link to cancer from chronic, occupational exposure to dimethylformamide.
ChEBI: A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.
The primary use of DMF is as a solvent with low evaporation rate. It is commonly used in industrial reactions and in laboratory that could be listed as follows:
|Bouveault aldehyde synthesis and Vilsmeier-Haack reaction
||As a reagent and another useful method of forming aldehydes.
|Recovery of olefins such as 1,3-butadiene via extractive distillation
|Manufacture of adhesives, synthetic leathers, fibers, films, pesticides and and surface coatings
|Synthesis of acyl halides
|Manufacture of solvent dyes
||Important raw material
|Compressing industrial acetylene to form a safe, concentrated solution
||A gas absorbent for separating and refining gases
||As a cleaning agent in wet synthetic leather production
||As a solvent in dry spinning of acrylic fibers
||As tin-plated parts quenching and circuit board cleaning agent
|Pesticide and Pharmaceutical industries
||An important intermediate of organic synthesis
|Separating and suspending carbon nanotubes
||Recommended by the NIST for use in near infrared spectroscopy
|Allowing for a quantitative determination of an unknown compound.
||As a standard in proton NMR spectroscopy
|Synthesis of organometallic compounds
||A source of carbon monoxide ligands
|Solvothermal synthesis of Metal Organic Frameworks
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 [Bretherick, 5th ed., 1995, p. 453]. Oxidation by chromium trioxide or potassium permanganate may lead to explosion [Pal B. C. et al., Chem. Eng. News, 1981, 59, p. 47].
Air & Water Reactions
Flammable. Water soluble.
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.
After that, different synthesis methods using a variety of raw materials have been developed, such as the dimethylamine-carbon monoxide method, the formamide-dimethylamine method, Hydrocyanic acid-methanol method, acetonitrile-methanol method, methyl formate-dimethylamine method, trichloroacetaldehyde-dimethylamine method, and the like. However, the current industrial production is still dominated by the dimethylamine-carbon monoxide method. The major production methods are concluded as follows:
1. Methyl formate-dimethylamine method: Esterification of formic acid with methanol to produce methyl formate, followed by reaction with dimethylamine in the gas phase to produce dimethylformamide, and distillation followed by recovery of methanol and unreacted methyl formate to reduce Pressure rectification products.
2. Dimethylamine-Carbon Monoxide Method: Obtained directly from the reaction of dimethylamine and carbon monoxide in the presence of sodium methoxide. The reaction conditions are 1.5-2.5 MPa and 110-150°C. The crude product is obtained through rectification to obtain the finished product.
3. Induce carbonyl synthesis of methyl monoxide and methanol at high pressure and 80-100 °C temperature to produce methyl formate, and then reacts with dimethylamine to produce dimethylformamide. After distillation, the finished product is obtained.
4. Obtained from the reaction of trichloroacetaldehyde and dimethylamine.