| Identification | Back Directory | [Name]
TERT-BUTYLDIMETHYLSILYL CYANIDE | [CAS]
56522-24-8 | [Synonyms]
T-BUTYLDIMETHYLSILYLNITRILE
TERT-BUTYLDIMETHYLSILYLNITRILE
TERT-BUTYLDIMETHYLSILYL CYANIDE
TERT-BUTYL-CYANO-DIMETHYLSILANE
tert-ButyldiMethylsilyl cyanide 97%
tert-butyldiMethylsilanecarbonitrile
[tert-butyl(dimethyl)silyl]formonitrile
Silanecarbonitrile, (1,1-dimethylethyl)dimethyl- | [Molecular Formula]
C7H15NSi | [MDL Number]
MFCD00054923 | [MOL File]
56522-24-8.mol | [Molecular Weight]
141.29 |
| Chemical Properties | Back Directory | [Melting point ]
76-79 °C (lit.) | [Boiling point ]
163-165°C | [density ]
0.815±0.06 g/cm3(Predicted) | [Fp ]
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 |
| Hazard Information | Back Directory | [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. |
|
| Company Name: |
Energy Chemical
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| Tel: |
021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Sigma-Aldrich
|
| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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