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氰化三甲基硅烷

产品号 A19598 公司名称 Alfa Aesar
CAS号 7677-24-9 公司网站 http://www.alfa.com
分子式 C4H9NSi 电 话
分子量 99.20646 传 真
纯 度 97% 电子邮件
保 存 Chembase数据库ID: 21464

产品价格信息

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产品别名

标题
Trimethylsilyl cyanide
IUPAC标准名
trimethylsilanecarbonitrile
IUPAC传统名
trimethylsilyl cyanide
别名
Cyanotrimethylsilane
TMSCN

产品登记号

EC号 231-657-3
Beilstein号 1737612
CAS号 7677-24-9
MDL号 MFCD00001765

产品性质

GHS警示性声明 P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
危险公开号 11-26/27/28-29-50/53
安全公开号 16-28-36/37/39-45-60-61
保存注意事项 Moisture Sensitive
TSCA收录
联合国危险货物等级 6.1
联合国危险货物编号 UN3383
联合国危险货物包装类别(PG) I
GHS危险品标识 GHS02
GHS危险品标识 GHS06
GHS危险品标识 GHS09
GHS危险声明 H225-H300-H310-H330-H400-H410
欧盟危险性物质标志 剧毒(Highly toxic) 剧毒(Highly toxic) (T+)
欧盟危险性物质标志 易燃性(Flammable) 易燃性(Flammable) (F)
欧盟危险性物质标志 环境危害性(Nature polluting) 环境危害性(Nature polluting) (N)
纯度 97%
沸点 118-119°C
密度 0.783
闪点 1°C(33°F)
熔点 11-12°C
折射率 1.3910

产品详细信息

参考文献

  • Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.
  • 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 examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).
  • For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).
  • 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).
  • For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).