3-(4-Bromophenyl)propionitrile

Base Information

• Chemical Name: 3-(4-Bromophenyl)propionitrile
• CAS No.: 57775-08-3
• Molecular Formula: C9H8BrN
• Molecular Weight: 210.073
• Hs Code.: 2926909090
• European Community (EC) Number: 673-011-7
• DSSTox Substance ID: DTXSID60370832
• Nikkaji Number: J918.731F
• Wikidata: Q72511226
• Mol file: 57775-08-3.mol

Synonyms:3-(4-Bromophenyl)propionitrile;3-(4-bromophenyl)propanenitrile;57775-08-3;3-(4-Bromo-phenyl)-propionitrile;4-Bromobenzenepropanenitrile;3-(p-bromophenyl)propionitrile;SCHEMBL2026682;DTXSID60370832;QAWLKTDBUQOFEF-UHFFFAOYSA-N;L-HISTIDINEMONOHYDROCHLORIDE;MFCD01310795;AKOS009159045;TS-02987;3-(4-bromophenyl)propionitrile, AldrichCPR;A8227;CS-0158403;FT-0640484;EN300-178112;O10869;A831599

Chemical Property of 3-(4-Bromophenyl)propionitrile

Chemical Property:

• Vapor Pressure: 0.00021mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 326.9°Cat760mmHg
• Flash Point: 151.5°C
• PSA: 23.79000
• Density: 1.416g/cm³
• LogP: 2.90528
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 208.98401
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

98%min ^*data from raw suppliers

3-(4-Bromophenyl)propionitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-52
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC#N)Br

Technology Process of 3-(4-Bromophenyl)propionitrile

There total 18 articles about 3-(4-Bromophenyl)propionitrile 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: 85.0%

acrylonitrile (107-13-1,25014-41-9) + (4-bromophenyl)hydrazine (589-21-9) → bromobenzene (108-86-1,52753-63-6) + 3-(4-Bromo-phenyl)-propionitrile (57775-08-3)

Guidance literature:

With copper(II) sulfate; In water; acetic acid; for 1h;

DOI:10.1016/S0040-4039(01)80781-4

Reference yield: 83.0%

trimethylsilyl cyanide (7677-24-9) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 3-(4-Bromo-phenyl)-propionitrile (57775-08-3)

Guidance literature:

2-(4-bromophenyl)-acetic acid; With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; iodine; In chloroform; at 60 ℃; Inert atmosphere;

trimethylsilyl cyanide; With tetrabutyl ammonium fluoride; In tetrahydrofuran; chloroform; at 60 ℃; for 5h; Reagent/catalyst; chemoselective reaction; Inert atmosphere;

DOI:10.1055/s-0033-1339903

Reference yield: 82.0%

2-cyano-3-(4-bromophenyl)propionitrile (21456-03-1) → 3-(4-Bromo-phenyl)-propionitrile (57775-08-3)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; 2,4,6-collidine hydrochloride; zinc(II) chloride; zinc; In tetrahydrofuran; at 35 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201908372

upstream raw materials:

1-bromo-4-(2-bromoethyl)benzene

sodium cyanide

acrylonitrile

(4-bromophenyl)hydrazine

Downstream raw materials:

C₂₂H₂₂N₂O₂

N,N'-Bis-<3-(p-bromphenyl)propyl>-thioharnstoff

2-(4-bromobenzyl)-3-oxopentanenitrile

3-(4-bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidine

Refernces

• 1、 Afanasyev, Oleg I.,Zarochintsev, Alexander,Petrushina, Tatiana,Cherkasova, Anastasia,Denisov, Gleb,Cherkashchenko, Ilia,Chusova, Olga,Jinho, Oh,Man-Seog, Chun,Usanov, Dmitry L.,Semenov, Sergei E.,Chusov, Denis. "Synthesis of Nitriles from Aldehydes with Elongation of the Molecule with Two Carbon Atoms". supporting information. p. 32 - 35. Retrieved 2018/12/05.
• 2、 Iwata,Tanaka,Kubosaki,Morita,Yoshimi. "A strategy for generating aryl radicals from arylborates through organic photoredox catalysis: Photo-Meerwein type arylation of electron-deficient alkenes". supporting information. p. 1257 - 1260. Retrieved 2018/02/09.