物质信息
ID:719733
名称和标识
IUPAC传统名
trimethylsilyl cyanide
IUPAC标准名
trimethylsilanecarbonitrile
别名
CyanotrimethylsilaneTMSCNTrimethylsilyl cyanide氰化三甲基硅烷
化合物性质
理化性质
密度
0.783
沸点
118-119°C
熔点
11-12°C
折射率
1.3910
闪点
1°C(33°F)
安全信息
GHS危险品标识
对水环境的危害
急性危害，类别1
慢性危害，类别1,2
急性毒性（口服，皮肤接触，吸入），类别1,2,3
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
剧毒 (T+)
易燃性 (F)
环境危害性 (N)联合国危险货物编号
UN3383
GHS警示性声明
P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
联合国危险货物等级
6.1
联合国危险货物包装类别(PG)
I
危险公开号
11-26/27/28-29-50/53
GHS危险声明
H225-H300-H310-H330-H400-H410
TSCA收录
是
安全公开号
16-28-36/37/39-45-60-61
保存注意事项
Moisture Sensitive
产品相关信息
纯度
97%
描述信息
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分子图谱
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参考文献
• Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.
• Tertiary alkyl halides normally undergo elimination when treated with alkali cyanides, but can be converted to the corresponding nitriles by reaction with TMSCN in the presence of SnCl4: Angew. Chem. Int. Ed., 20, 1017 (1981).
• Reacts with epoxides in the presence of ZnI2 to give trans-ɑ-siloxy isocyanides, which can be readily hydrolyzed to the hydroxy isocyanides: J. Am. Chem. Soc., 104, 5849 (1982); Org. Synth. Coll., 7, 294 (1990). In the presence of Ag salts (AgClO4, AgBF4 or AgOTf), alkenes can be converted to isocyanides in Markovnikov fashion: Synlett, 288 (1999).
• The ZnI2-catalyzed procedure allows cyanohydrins of unreactive ketones to be prepared in good yield, avoiding the unfavourable equilibria often encountered with the classical alkali cyanide method. For details and list of examples, see: Org. Synth. Coll., 7, 20 (1990). Other catalysts including Et3N or Bu3P are also effective: Chem. Lett., 537, 541 (1991). For catalysis by Methyl triphenylphosphonium iodide, A15644, see: Tetrahedron Lett., 44, 6157 (2003). In the absence of a catalyst, aldehydes have been found to give good yields of the TMS cyanohydrin, but reaction with ketones is very slow: J. Chem. Soc., Perkin 1, 2383 (1995). For use of Tetracyanoethylene, A13945, as a c-acid catalyst for both aldehydes and ketones, see: J. Chem. Soc., Perkin 1, 2155 (1995). Under the same conditions, dimethyl acetals give O-methyl cyanohydrins.
• For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).
• For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).
• For examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).