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| | TERT-BUTYLDIMETHYLSILYL CYANIDE Basic information |
| Product Name: | TERT-BUTYLDIMETHYLSILYL CYANIDE | | Synonyms: | T-BUTYLDIMETHYLSILYLNITRILE;TERT-BUTYLDIMETHYLSILYL CYANIDE;TERT-BUTYL-CYANO-DIMETHYLSILANE;TERT-BUTYLDIMETHYLSILYLNITRILE;tert-ButyldiMethylsilyl cyanide 97%;[tert-butyl(dimethyl)silyl]formonitrile;tert-butyldiMethylsilanecarbonitrile;Silanecarbonitrile, (1,1-dimethylethyl)dimethyl- | | CAS: | 56522-24-8 | | MF: | C7H15NSi | | MW: | 141.29 | | EINECS: | | | Product Categories: | | | Mol File: | 56522-24-8.mol |  |
| | TERT-BUTYLDIMETHYLSILYL CYANIDE Chemical Properties |
| 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 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 |
| | TERT-BUTYLDIMETHYLSILYL CYANIDE Usage And Synthesis |
| Physical properties | bp 163–167°C/760 mmHg; mp 76–78°C. | | 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). | | Uses | 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. |
| | TERT-BUTYLDIMETHYLSILYL CYANIDE Preparation Products And Raw materials |
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