Substance
ID:716419
Names and Identifiers
IUPAC name
N,N-dimethylformamide
IUPAC Traditional name
dimethylformamide
Synonyms
DMFN,N-二甲基甲酰胺N,N-Dimethylformamide
Registration numbers
Beilstein Number
MDL Number
Merck Index
EC Number
CAS Number
Properties
Safety Information
GHS Pictograms
Respiratory sensitization, category 1
Germ cell mutagenicity, categories 1A,1B,2
Carcinogenicity, categories 1A,1B,2
Reproductive toxicity, categories 1A,1B,2
Specific Target Organ Toxicity – Single exposure, categories 1,2
Specific Target Organ Toxicity – Repeated exposure, categories 1,2
Aspiration Hazard, category 1
Flammable gases, category 1
Flammable aerosols, categories 1,2
Flammable liquids, categories 1,2,3
Self-reactive substances and mixtures, Types B,C,D,E,F
Pyrophoric liquids, category 1
Pyrophoric solids, category 1
Self-heating substances and mixtures
Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3
Organic peroxides, Types B,C,D,E,F
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
European Hazard Symbols
Toxic (T)Packing Group
III
GHS Precautionary statements
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
Risk Statements
61-20/21-36
Safety Statements
53-45
TSCA Listed
是
UN Number
UN2265
RTECS
LQ2100000
Hazard Class
3
GHS Hazard statements
H360-H226-H312-H332-H319
Physical Property
Melting Point
-61°C
Density
0.944
Flash Point
57°C(135°F)
Boiling Point
153°C
Refractive Index
1.4310
Product Information
Purity
99%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.
• In combination with POCl3, (COCl)2, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:
• DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).
• Vilsmeier conditions also promote dehydrations, e.g. in cyclodehydration of hydroxyphenols to give cyclic ethers, as an efficient alternative to the Mitsunobu reaction: J. Chem. Soc., Perkin 1, 2249 (1996); J. Org. Chem., 59, 4346 (1994):
• Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.
• Compare also N-Methylformanilide, A11829, and preformed Vilsmeier reagent (Chloromethylene)dimethylammonium chloride, B24172. Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994). Formylation can be extended to less active substrates, e.g. acenaphthene or mesitylene, with the DMF-triflic anhydride reagent: J. Chem. Soc., Chem. Commun., 1571 (1990). Under Vilsmeier conditions, electron-rich alkenes can be converted to ɑ?-unsaturated aldehydes; see, e.g.: Synthesis, 752 (1976); and ketones to ?-chloroenals: Synthesis, 496 (1985); Org. Synth. Coll., 5, 215 (1973).
• In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).
• For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.