FComEx: N,N-Dimethylformamide (PC000826)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:57 UTC

Update date

2017-01-19 02:36:37 UTC

FoodComEx ID

PC000826

FoodDB Record

FDB004724

Chemical Information

Name

N,N-Dimethylformamide

Description

Dimethylformamide is a polar (hydrophilic) Aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions. Dimethylformamide can be synthesized from methyl formate and dimethyl amine or reaction of dimethyl amine and carbon monoxide. 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.; Dimethylformamide is the organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated DMF (though this acronym is sometimes used for dimethylfuran), this colourless liquid is miscible with water and the 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. Its name is derived from the fact that it is a derivative of formamide, the amide of formic acid.; 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. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals.; The world-wide consumption of DMF in 2001 was approximately 285,000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). 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. (PMID: 17254560). N,N-Dimethylformamide is found in papaya.

CAS Number

68-12-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Dimethyl formamide	biospider
Dimethyl-formamide	biospider
Dimethylamid kyseliny mravenci	biospider
Dimethylforamide	biospider
Dimethylformamid	biospider
Dimethylformamid (german)	biospider
Dimethylformamide	biospider
Dimetilformamide	biospider
Dimetylformamidu	biospider
DMF	biospider
DMF (amide)	biospider
DMF (dimethylformamide)	biospider
DMF (van)	biospider
DMFA	biospider
Dwumetyloformamid	biospider
Dynasolve 100	biospider
Formamide, dimethyl-	biospider
Formamide, n,n-dimethyl-	biospider
Formic acid, amide, n,n-dimethyl-	biospider
Formin acid,amide,n,n-dimethyl	biospider
Formyldimethylamine	biospider
HCON(CH3)2	biospider
HSDB 78	biospider
N-formyldimethylamine	biospider
N, n-dimethylmethanamide	biospider
N,n- dimethyl formamide	biospider
N,n- dimethylformamide	biospider
N,n-dimethyl formamide	biospider
N,N-Dimethyl-formamide	HMDB
N,n-dimethylformamide	biospider
N,N-Dimethylformamide [UN2265] [Flammable liquid]	biospider
N,n-dimethylmethanamide	biospider
N,n-dimetilformamida	biospider

Chemical Formula

C3H7NO

IUPAC name

N,N-dimethylformamide

InChI Identifier

InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3

InChI Key

ZMXDDKWLCZADIW-UHFFFAOYSA-N

Isomeric SMILES

CN(C)C=O

Average Molecular Weight

73.0938

Monoisotopic Molecular Weight

73.052763851

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Tertiary carboxylic acid amides

Alternative Parents

Substituents