TERT-BUTYLDIMETHYLSILYL CYANIDE
Synonym(s):tert-Butyl-cyano-dimethylsilane
- CAS NO.:56522-24-8
- Empirical Formula: C7H15NSi
- Molecular Weight: 141.29
- MDL number: MFCD00054923
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-03-20 14:21:42
What is TERT-BUTYLDIMETHYLSILYL CYANIDE?
Physical properties
bp 163–167°C/760 mmHg; mp 76–78°C.
The Uses of TERT-BUTYLDIMETHYLSILYL CYANIDE
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).
The Uses of TERT-BUTYLDIMETHYLSILYL CYANIDE
tert-Butyldimethylsilyl cyanide may be used as reagent for the formation of β-isonitrile alcohols via epoxides.
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.
Properties of TERT-BUTYLDIMETHYLSILYL CYANIDE
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 information for TERT-BUTYLDIMETHYLSILYL CYANIDE
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. |
Computed Descriptors for TERT-BUTYLDIMETHYLSILYL CYANIDE
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