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Trimethylsilyl cyanide

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Trimethylsilyl cyanide
Names
IUPAC name
trimethylsilylformonitrile
Other names
Cyanotrimethylsilane; TMS cyanide; Trimethylsilylnitrile; Trimethylsilanecarbonitrile' Trimethylsilylcarbonitrile
Identifiers
3D model (JSmol)
Abbreviations TMSCN
ChemSpider
ECHA InfoCard 100.028.780 Edit this at Wikidata
  • InChI=1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3 checkY
    Key: LEIMLDGFXIOXMT-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NSi/c1-6(2,3)4-5/h1-3H3
    Key: LEIMLDGFXIOXMT-UHFFFAOYAM
  • C[Si](C)(C)C#N
Properties
C4H9NSi
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)
reacts with water
Solubility organic solvents
1.392
Hazards
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).
checkY verify (what is checkY☒N ?)

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

In its principal reaction, 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.

Safety

Trimethylsilyl cyanide is treated with care since it hydrolyzes to give hydrogen cyanide:

2 (CH3)3SiCN + H2O → (CH3)3SiOSi(CH3)3 + 2 HCN

References

  1. ^ Livinghouse, T. (1990). "Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone". Organic Syntheses; Collected Volumes, vol. 7, p. 517.
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