Trimethylsilyl cyanide

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Trimethylsilyl cyanide
IUPAC name
Other names
Cyanotrimethylsilane; TMS cyanide; Trimethylsilylnitrile; Trimethylsilanecarbonitrile' Trimethylsilylcarbonitrile
  • 7677-24-9 ☑Y
3D model (JSmol)
  • Interactive image
Abbreviations TMSCN
  • 74110 ☑Y
ECHA InfoCard 100.028.780
PubChem CID
  • 82115
Molar mass 99.208 g·mol−1
Density 0.793 g/mL at 20 °C
Melting point 8 to 11 °C (46 to 52 °F; 281 to 284 K)
Boiling point 114 to 117 °C (237 to 243 °F; 387 to 390 K)
Solubility organic solvents
R-phrases (outdated) R11 R26/27/28 R29
S-phrases (outdated) S16 S36/37/39 S45
Flash point 1 °C (34 °F; 274 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:[1]

LiCN + (CH3)3SiCl → (CH3)3SiCN + LiCl


The molecule exhibits the expected structure of a nitrile-like compound. The compound exists in a facile equilibrium with a small amount of the isomeric isocyanide (CH3)3SiNC.[2] By contrast, the nearly isostructural tert-butyl nitrile does not readily isomerize to tert-butyl isocyanide.


Trimethylsilyl cyanide hydrolyzes to give hydrogen cyanide:

(CH3)3SiCN + H2O → (CH3)3SiOH + HCN

In its principal application, it adds across carbon-oxygen double bonds, for example in an aldehyde:

RCHO + (CH3)3SiCN → RCH(CN)OSi(CH3)3

The product is an O-silylated cyanohydrin.

One use of this reagent is to convert pyridine-N-oxides into 2-cyanopyridine. This transformation is best done in dichloromethane solution using dimethylcarbamoyl chloride as the activating electrophile. It is possible to use benzoyl chloride but the yields and regioselectivity of the addition of the cyano group are lower.


This chemical is rated as "Fatal if swallowed, in contact with skin or if inhaled" as it hydrolyzes in the presence of moisture to give hydrogen cyanide gas.


  1. ^ Livinghouse, T. (1990). "Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone". Organic Syntheses.; Collective Volume, 7, p. 517
  2. ^ Booth, M. R.; Frankiss, S. G. (1968). "Trimethylsilyl isocyanide". Chem. Commun. (21): 1347–1348. doi:10.1039/C19680001347.
Retrieved from ""
This content was retrieved from Wikipedia :
This page is based on the copyrighted Wikipedia article "Trimethylsilyl cyanide"; it is used under the Creative Commons Attribution-ShareAlike 3.0 Unported License (CC-BY-SA). You may redistribute it, verbatim or modified, providing that you comply with the terms of the CC-BY-SA