物质信息
ID:716419
名称和标识
IUPAC标准名
N,N-dimethylformamide
IUPAC传统名
dimethylformamide
别名
DMFN,N-二甲基甲酰胺N,N-Dimethylformamide
化合物性质
理化性质
密度
0.944
闪点
57°C(135°F)
折射率
1.4310
熔点
-61°C
沸点
153°C
安全信息
联合国危险货物编号
UN2265
GHS危险品标识
急性毒性（口服，皮肤接触，吸入），类别4
皮肤刺激，类别2
眼刺激，类别2
皮肤过敏，类别1
特定目标器官毒性 -一次接触，类别3
呼吸道过敏，类别1
生殖细胞突变，类别1A，1B，2
致癌性，类别1A，1B，2
生殖毒性，类别1A，1B，2
特定目标器官毒性 – 一次接触，类别1,2
特定目标器官毒性 – 反复接触，类别1,2
吸入危险，类别1
易燃气体类别1
易燃气溶胶，第1,2类
易燃液体，类别1,2,3
自反应物质和混合物，类型B，C，D，E，F
自燃液体类别1
自燃固体类别1
自我放热物质和混合物，类别1,2
与水接触的物质和混合物，放出易燃气体类别1,2,3
有机过氧化物，类别B，C，D，E，F
欧盟危险性物质标志
有毒 (T)RTECS编号
LQ2100000
联合国危险货物等级
3
GHS危险声明
H360-H226-H312-H332-H319
GHS警示性声明
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
安全公开号
53-45
TSCA收录
是
危险公开号
61-20/21-36
联合国危险货物包装类别(PG)
III
产品相关信息
纯度
99%
描述信息
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分子图谱
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参考文献
• 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).
• 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).
• 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):
• In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).
• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.
• For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.