N,N-Dimethylformamide

• Catalog No.: A13547
• CAS Number: 68-12-2
• M. F.: C3H7NO
• M. W.: 73.09378
• Purity: 99%

SYNONYMS

• Title: N,N-二甲基甲酰胺
• IUPAC name: N,N-dimethylformamide
• IUPAC Traditional name: dimethylformamide
• Synonyms: DMF

DATABASE IDS

• MDL Number: MFCD00003284
• EC Number: 200-679-5
• Merck Index: 143243
• Beilstein Number: 605365
• CAS Number: 68-12-2

PROPERTIES

• Boiling Point: 153°C
• Density: 0.944
• Flash Point: 57°C(135°F)
• Melting Point: -61°C
• Refractive Index: 1.4310
• GHS Hazard statements: H360-H226-H312-H332-H319
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 61-20/21-36
• RTECS: LQ2100000
• Safety Statements: 53-45
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2265
• Packing Group: III
• Purity: 99%

REFERENCES

• Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.
• In combination with POCl₃, (COCl)₂, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:
  
• 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).
• 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):
  
• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.
• DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).
• 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.