N,N-二甲基甲酰胺

• 产品号: A13547
• CAS号: 68-12-2
• 分子式: C3H7NO
• 分子量: 73.09378
• 纯 度: 99%

产品别名

• 标题: N,N-Dimethylformamide
• IUPAC标准名: N,N-dimethylformamide
• IUPAC传统名: dimethylformamide
• 别名: DMF

产品登记号

• MDL号: MFCD00003284
• EC号: 200-679-5
• 默克索引号: 143243
• Beilstein号: 605365
• CAS号: 68-12-2

产品性质

• 沸点: 153°C
• 密度: 0.944
• 闪点: 57°C(135°F)
• 熔点: -61°C
• 折射率: 1.4310
• GHS危险声明: H360-H226-H312-H332-H319
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• 危险公开号: 61-20/21-36
• RTECS编号: LQ2100000
• 安全公开号: 53-45
• TSCA收录: 是
• 联合国危险货物等级: 3
• 联合国危险货物编号: UN2265
• 联合国危险货物包装类别(PG): III
• 纯度: 99%

参考文献

• 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.