Trimethylsilyl cyanide

• Catalog No.: A19598
• CAS Number: 7677-24-9
• M. F.: C4H9NSi
• M. W.: 99.20646
• Purity: 97%

SYNONYMS

• Title: 氰化三甲基硅烷
• IUPAC name: trimethylsilanecarbonitrile
• IUPAC Traditional name: trimethylsilyl cyanide
• Synonyms: Cyanotrimethylsilane; TMSCN

DATABASE IDS

• EC Number: 231-657-3
• Beilstein Number: 1737612
• CAS Number: 7677-24-9
• MDL Number: MFCD00001765

PROPERTIES

• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
• Risk Statements: 11-26/27/28-29-50/53
• Safety Statements: 16-28-36/37/39-45-60-61
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN3383
• Packing Group: I
• GHS Hazard statements: H225-H300-H310-H330-H400-H410
• European Hazard Symbols: Highly toxic (T+)
• European Hazard Symbols: Flammable (F)
• European Hazard Symbols: Nature polluting (N)
• Purity: 97%
• Boiling Point: 118-119°C
• Density: 0.783
• Flash Point: 1°C(33°F)
• Melting Point: 11-12°C
• Refractive Index: 1.3910

REFERENCES

• 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).