TERT-BUTYLDIMETHYLSILYL CYANIDE Property

Melting point:

76-79 °C (lit.)

Boiling point:

163-165°C

Density 

0.815±0.06 g/cm3(Predicted)

Flash point:

45°C

solubility 

sol organic solvents (methylene chloride, THF, chloroform); reacts rapidly with water and protic solvents.

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

2234709

Safety

Hazard Codes 

T

Risk Statements 

23/24/25

Safety Statements 

36/37/39-45

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

F 

10-21

TSCA 

No

HazardClass 

6.1(b)

PackingGroup 

III

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

TERT-BUTYLDIMETHYLSILYL CYANIDE Chemical Properties,Usage,Production

Physical properties

bp 163–167°C/760 mmHg; mp 76–78°C.

Uses

tert-Butyldimethylsilyl cyanide may be used as reagent for the formation of β-isonitrile alcohols via epoxides.

Uses

The Lewis acid-catalyzed reaction of t-butyldimethylsilyl cyanide(TBDMSCN)with aldehydes and ketones affords the corresponding silylated cyanohydrins in good yield (eq 1).These have a greater stability than the silylated cyanohydrins obtained by using cyanotrimethylsilane The addition of TBDMSCN to sterically hindered ketones proceeds smoothly in the presence of a catalytic amount of zinc iodide or potassium cyanide/18-crown-6 (eqs 2–4).Achelation-controlled stereoselective synthesis of silylated cyanohydrins has also been reported (eq 5).

Preparation

conveniently prepared by refluxing t-butyldimethylchlorosilane (1 equiv), potassium cyanide (1.3 equiv) and 18-crown-6 (0.31 equiv) in dry methylene chloride under nitrogen.The reagent can also be prepared by the reaction of silver(I) cyanide with t-butyldimethylchlorosilane, or stirring at 60°C for 4 h a mixture of sodium cyanide, Amberlite XAD-4 resin, and t-butyldimethylchlorosilane in acetonitrile

General Description

tert-Butyldimethylsilyl cyanide (TBDMSCN) is a bulkier trialkylsilylcyanide. It participates in the cyanosilylation of enantiopure 4-oxoazetidine-2-carbaldehydes. Addition of TBDMSCN to sterically hindered ketones in the presence of Lewis acid or base catalyst has been studied. ZnI₂-catalyzed addition of TBDSCN to 2,2-dimethylcyclohexanone, 2,2,6-trimethylcyclohexanone and 2,2,6,6-tetramethylcyclohexanone affords protected cyanohydrins.