tert-Butyldimethylsilyl cyanide

Base Information

• Chemical Name: tert-Butyldimethylsilyl cyanide
• CAS No.: 56522-24-8
• Molecular Formula: C7H15NSi
• Molecular Weight: 141.288
• European Community (EC) Number: 628-034-7
• DSSTox Substance ID: DTXSID90404114
• Nikkaji Number: J514.416G
• Wikidata: Q82208113
• Mol file: 56522-24-8.mol

Synonyms:tert-Butyldimethylsilyl cyanide;56522-24-8;[tert-butyl(dimethyl)silyl]formonitrile;tert-Butyl-cyano-dimethylsilane;tert-butyldimethylsilanecarbonitrile;Silanecarbonitrile, (1,1-dimethylethyl)dimethyl-;t-butyldimethylsilylnitrile;t-butyldimethylsilyl cyanide;SCHEMBL563270;tert-Butyldimethylsilyl nitrile;DTXSID90404114;tert-Butyldimethylsilyl cyanide, 97%;AKOS015950628

Chemical Property of tert-Butyldimethylsilyl cyanide

Chemical Property:

• Vapor Pressure: 1.78mmHg at 25°C
• Melting Point: 76-79 °C(lit.)
• Refractive Index: 1.411
• Boiling Point: 166.4 °C at 760 mmHg
• Flash Point: 54.5 °C
• PSA: 23.79000
• Density: 0.815 g/cm³
• LogP: 2.55768
• Solubility.: sol organic solvents (methylene chloride, THF, chloroform); reacts rapidly with water and protic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 141.097376017
• Heavy Atom Count: 9
• Complexity: 144

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyldimethylsilyl cyanide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)C#N
• 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). tert-Butyldimethylsilyl cyanide may be used as reagent for the formation of β-isonitrile alcohols via epoxides.

Technology Process of tert-Butyldimethylsilyl cyanide

There total 6 articles about tert-Butyldimethylsilyl cyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trimethylsilyl cyanide (7677-24-9) + tert-butyldimethylsilyl chloride (18162-48-6) → chloro-trimethyl-silane (75-77-4) + tert-butyldimethylsilyl cyanide (56522-24-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; at 100 - 180 ℃; for 4h;

Reference yield: 89.0%

potassium cyanide (151-50-8) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl cyanide (56522-24-8)

Guidance literature:

With 18-crown-6 ether; In dichloromethane; for 48h; Heating;

DOI:10.1021/jo00375a050

Reference yield: 85.0%

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl cyanide (56522-24-8)

Guidance literature:

With AMBERLITE XAD-4; sodium cyanide; In acetonitrile; at 60 ℃; for 4h;

DOI:10.1246/bcsj.60.2257

upstream raw materials:

silver(I) cyanide

tert-butyldimethylsilyl chloride

trimethylsilyl cyanide

lithium cyanide

Downstream raw materials:

1-tert-butyldimethylsilyloxy-2-methyl-1-cyclohexene

C₁₃H₁₉NO₄Si

C₄₉H₅₃N₃O₅Si

2-[(tert-butyldimethylsilyl)oxy]-2-(p-tolyl)acetonitrile

Refernces

• 1、 Huenig, Siegfried,Schaefer, Matthias. "Trimethylsilyl Cyanide - A Reagent for Umpolung, XX. - On the Regioselectivity of the Addition of Carbonyl Compounds to α,β-Unsaturated Aldehydes after Umpolung". . p. 177 - 190. Retrieved 2007/10/02.
• 2、 Sukata, Kazuaki. "A Convenient Method for the Synthesis of Alkylsilyl Cyanides Using Potassium or Sodium Cyanide Impregnated on Amberlite XAD Resin". . p. 2257 - 2258. Retrieved 2007/10/02.