56522-24-8 Usage
Description
TERT-BUTYLDIMETHYLSILYL CYANIDE, also known as t-butyldimethylsilyl cyanide (TBDMSCN), is a bulkier trialkylsilylcyanide that is widely utilized in various chemical reactions and processes due to its unique properties and reactivity. It is known for its ability to participate in the cyanosilylation of enantiopure 4-oxoazetidine-2-carbaldehydes and its smooth addition to sterically hindered ketones in the presence of a Lewis acid or base catalyst.
Physical properties:
TBDMSCN has a boiling point of 163–167°C at 760 mmHg and a melting point of 76–78°C.
Uses
Used in Chemical Synthesis:
TERT-BUTYLDIMETHYLSILYL CYANIDE is used as a reagent for the formation of silylated cyanohydrins through the Lewis acid-catalyzed reaction with aldehydes and ketones. These silylated cyanohydrins have a greater stability than those obtained using cyanotrimethylsilane.
Used in the Synthesis of β-Isonitrile Alcohols:
TERT-BUTYLDIMETHYLSILYL CYANIDE is used as a reagent for the formation of β-isonitrile alcohols via epoxides, which are important intermediates in organic synthesis.
Used in the Synthesis of Protected Cyanohydrins:
TERT-BUTYLDIMETHYLSILYL CYANIDE is used as a reagent in the synthesis of protected cyanohydrins through the addition to sterically hindered ketones in the presence of a catalytic amount of zinc iodide or potassium cyanide/18-crown-6. This process has been studied with various ketones, such as 2,2-dimethylcyclohexanone, 2,2,6-trimethylcyclohexanone, and 2,2,6,6-tetramethylcyclohexanone.
Used in the Pharmaceutical Industry:
TERT-BUTYLDIMETHYLSILYL CYANIDE is used as a reagent in the pharmaceutical industry for the synthesis of various drugs and drug candidates, taking advantage of its unique reactivity and stability in chemical reactions.
Used in the Chemical Research Industry:
TERT-BUTYLDIMETHYLSILYL CYANIDE is used as a research reagent for the development of new chemical processes and methodologies, as well as for the study of its reactivity and applications in various chemical reactions.
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
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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