Trimethylsilyl cyanide

Trimethylsilyl cyanide
Names
	Preferred IUPAC name Trimethylsilanecarbonitrile
	Other names Cyanotrimethylsilane; TMS cyanide; Trimethylsilylnitrile; Trimethylsilylcarbonitrile; Trimethylsilylformonitrile
Identifiers
CAS Number	7677-24-9 ;
3D model (JSmol)	Interactive image;
Abbreviations	TMSCN
ChemSpider	74110 ;
ECHA InfoCard	100.028.780
EC Number	231-657-3;
PubChem CID	82115;
CompTox Dashboard (EPA)	DTXSID9064766 ;
	InChI InChI=1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3 Key: LEIMLDGFXIOXMT-UHFFFAOYSA-N ; InChI=1/C4H9NSi/c1-6(2,3)4-5/h1-3H3 Key: LEIMLDGFXIOXMT-UHFFFAOYAM;
	SMILES C[Si](C)(C)C#N;
Properties
Chemical formula	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)
Solubility in water	hydrolyzes
Solubility	organic solvents
Refractive index (nD)	1.392
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H300, H310, H330, H410
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P310, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	1 °C (34 °F; 274 K)
Related compounds
Other anions	Trimethylsilyl chloride
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]^[2]

LiCN + (CH₃)₃SiCl → (CH₃)₃SiCN + LiCl

^ Livinghouse, T. (1981). "Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone". Organic Syntheses. 60: 126. doi:10.15227/orgsyn.060.0126.
^ Groutas, William C.; Jin, Zhendong; Zhang, Heng (2011). "Cyanotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc276.pub2. ISBN 978-0471936237.