1-(2-Bromophenyl)cyclopropanecarbonitrile

Base Information

• Chemical Name: 1-(2-Bromophenyl)cyclopropanecarbonitrile
• CAS No.: 124276-75-1
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.084
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID60601774
• Wikidata: Q82498591
• Mol file: 124276-75-1.mol

Synonyms:1-(2-Bromophenyl)cyclopropanecarbonitrile;124276-75-1;1-(2-BROMOPHENYL)CYCLOPROPANE-1-CARBONITRILE;1-(2-Bromo-phenyl)-cyclopropanecarbonitrile;Cyclopropanecarbonitrile, 1-(2-bromophenyl)-;MFCD07374407;SCHEMBL6898;DTXSID60601774;QGRRKIFTSXBLNX-UHFFFAOYSA-N;ZEA27675;AKOS012126346;AB39386;AS-41479;SY152440;DB-362719;CS-0088393;EN300-152374;A890531;Z1020847928

Chemical Property of 1-(2-Bromophenyl)cyclopropanecarbonitrile

Chemical Property:

• PSA: 23.79000
• LogP: 3.00428
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 220.98401
• Heavy Atom Count: 12
• Complexity: 223

Purity/Quality:

98%min ^*data from raw suppliers

1-(2-Bromophenyl)cyclopropanecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1(C#N)C2=CC=CC=C2Br

Technology Process of 1-(2-Bromophenyl)cyclopropanecarbonitrile

There total 9 articles about 1-(2-Bromophenyl)cyclopropanecarbonitrile 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%

2-(2-bromophenyl)acrylonitrile (1393491-97-8) + N,N-diethylethanaminium bis[benzene-1,2-diolato(2-)-kappa201,02](iodomethyl)silicate → 1-(2-bromophenyl)cyclopropane-1-carbonitrile (124276-75-1)

Guidance literature:

With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; In dimethyl sulfoxide; at 35 ℃; for 3h; chemoselective reaction; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/jacs.8b05243

Reference yield: 90.0%

2-(2-bromophenyl)acetonitrile (19472-74-3) + diphenyl(vinyl)sulfonium trifluoromethanesulfonate → 1-(2-bromophenyl)cyclopropane-1-carbonitrile (124276-75-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 21 ℃; for 12h;

DOI:10.1016/j.tetlet.2018.02.080

Reference yield: 85.0%

(Z)-2-(2-bromophenyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime → 1-(2-bromophenyl)cyclopropane-1-carbonitrile (124276-75-1)

Guidance literature:

(Z)-2-(2-bromophenyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime; With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Glovebox;

With lithium hexamethyldisilazane; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1055/s-0039-1690872

upstream raw materials:

2-(2-bromophenyl)acetonitrile

1-Bromo-2-chloroethane

2-(2-bromophenyl)acrylonitrile

1-(cyclopropylidenemethyl)-2-bromobenzene

Refernces

• 1、 Stead, Darren. "The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles". supporting information. . Retrieved 2020/09/04.
• 2、 Zhou, Mingwei,Hu, Yimin,En, Ke,Tan, Xuefei,Shen, Hong C.,Qian, Xuhong. "Efficient cyclopropanation of aryl/heteroaryl acetates and acetonitriles with vinyl diphenyl sulfonium triflate". supporting information. p. 1443 - 1445. Retrieved 2018/03/12.