56522-24-8 Usage
Physical properties
bp 163–167°C/760 mmHg; mp 76–78°C.
Uses
Different sources of media describe the Uses of 56522-24-8 differently. You can refer to the following data:
1. 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).
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 56522-24-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,5,2 and 2 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 56522-24:
(7*5)+(6*6)+(5*5)+(4*2)+(3*2)+(2*2)+(1*4)=118
118 % 10 = 8
So 56522-24-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H15NSi/c1-7(2,3)9(4,5)6-8/h1-5H3
56522-24-8Relevant articles and documents
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Treichel,P.M.,Shaw,D.B.
, p. 21 - 30 (1977)
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A Convenient Method for the Synthesis of Alkylsilyl Cyanides Using Potassium or Sodium Cyanide Impregnated on Amberlite XAD Resin
Sukata, Kazuaki
, p. 2257 - 2258 (2007/10/02)
Potassium and sodium cyanide impregnated on Amberlite XAD resin were found to be effective for converting alkylsilyl chloride to the corresponding alkylsilyl cyanide under mild conditions.
Epoxide Opening with tert-Butyldimethylsilyl Cyanide-Zinc Iodide. Evidence for a Stepwise Process in the Opening of a Sterically Hindered Epoxide
Gassman, Paul G.,Haberman, Leonard M.
, p. 5010 - 5013 (2007/10/02)
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