4-(Trimethylsilyl)benzonitrile

Base Information

• Chemical Name: 4-(Trimethylsilyl)benzonitrile
• CAS No.: 17921-68-5
• Molecular Formula: C10H13 N Si
• Molecular Weight: 175.305
• Hs Code.: 2931900090
• European Community (EC) Number: 807-324-9
• DSSTox Substance ID: DTXSID80474028
• Nikkaji Number: J792.272H
• Wikidata: Q82303793
• Mol file: 17921-68-5.mol

Synonyms:17921-68-5;4-(TRIMETHYLSILYL)BENZONITRILE;4-trimethylsilylbenzonitrile;Benzonitrile, 4-(trimethylsilyl)-;4-Trimethlysilanylbenzonitrile;SCHEMBL1161032;DTXSID80474028;VLMZJZUVZAHCFT-UHFFFAOYSA-N;MFCD09039085;AKOS006331715;AS-2951;CS-0377310

Chemical Property of 4-(Trimethylsilyl)benzonitrile

Chemical Property:

• Boiling Point: 245.1°Cat760mmHg
• Flash Point: 102°C
• PSA: 23.79000
• Density: 0.94g/cm³
• LogP: 2.10348
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 175.081725953
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99.0%Min ^*data from raw suppliers

4-(Trimethylsilyl)benzonitrile >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C1=CC=C(C=C1)C#N

Technology Process of 4-(Trimethylsilyl)benzonitrile

There total 15 articles about 4-(Trimethylsilyl)benzonitrile 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: 95.0%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) + 4-bromobenzenecarbonitrile (623-00-7) → (4-cyanophenyl)trimethylsilane (17921-68-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 160 ℃; for 96h;

DOI:10.1016/0022-328X(93)80045-D

Reference yield: 88.0%

zinc(II) cyanide (557-21-1) + 4-chlorophenyltrimethylsilane (10557-71-8) → (4-cyanophenyl)trimethylsilane (17921-68-5)

Guidance literature:

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc; In acetonitrile; at 60 ℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b00732

Reference yield: 81.0%

4-Cyanochlorobenzene (623-03-0) + 1,1,1,2,2,2-hexamethyldisilane (1450-14-2) → (4-cyanophenyl)trimethylsilane (17921-68-5)

Guidance literature:

With water; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃; for 24h;

DOI:10.1021/ol701518f

upstream raw materials:

terephthalonitrile

1,1,1,2,2,2-hexamethyldisilane

chloro-trimethyl-silane

4-bromobenzenecarbonitrile

Downstream raw materials:

benzonitrile

4-iodobenzonitrile

4-trimethylsilylbenzaldehyde

3,4-Dibromo-1-(4-trimethylsilanyl-benzyl)-pyrrole-2,5-dione

Refernces

• 1、 Hitoshio, Kenshiro,Yamagishi, Hiroki,Shimokawa, Jun,Yorimitsu, Hideki. "Sodium silylsilanolate enables nickel-catalysed silylation of aryl chlorides". supporting information. p. 6867 - 6870. Retrieved 2021/07/19.
• 2、 Ueda, Yohei,Tsujimoto, Nagataka,Yurino, Taiga,Tsurugi, Hayato,Mashima, Kazushi. "Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile: Via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine". . p. 994 - 999. Retrieved 2019/02/03.