4-Cyanobenzyl bromide

Base Information

• Chemical Name: 4-Cyanobenzyl bromide
• CAS No.: 17201-43-3
• Molecular Formula: C8H6BrN
• Molecular Weight: 196.046
• Hs Code.: 29269090
• European Community (EC) Number: 241-246-0
• NSC Number: 95792
• UNII: RV332B84ZG
• DSSTox Substance ID: DTXSID40864744
• Nikkaji Number: J266.795I
• Wikidata: Q72457942
• Mol file: 17201-43-3.mol

Synonyms:4-Cyanobenzyl bromide;17201-43-3;4-(Bromomethyl)benzonitrile;p-Cyanobenzyl bromide;Benzonitrile, 4-(bromomethyl)-;alpha-Bromo-p-tolunitrile;4-bromomethylbenzonitrile;4-Bromomethyl-benzonitrile;alpha-Bromo-p-toluonitrile;p-(Bromomethyl)benzonitrile;Benzonitrile, p-(bromomethyl)-;.alpha.-Bromo-p-tolunitrile;4-cyanobenzylbromide;NSC 95792;p-Tolunitrile, alpha-bromo-;p-Toluonitrile, alpha-bromo-;RV332B84ZG;p-Tolunitrile, .alpha.-bromo-;p-Toluonitrile, .alpha.-bromo-;EINECS 241-246-0;NSC-95792;4-Cyano benzyl bromide;4CNBB;A-BROMO-P-TOLUNITRILE;AKOS BC-3028;1-(bromomethyl)-4-cyanobenzene;p-cyanobenzylbromide;4-cyano benzylbromide;4-cyano-benzylbromide;4-cyanobenzyl-bromide;a-bromo p-tolunitrile;a-bromo-p-toluonitrile;p-cyano-benzyl bromide;4-cyano-benzyl bromide;para-cyanobenzyl bromide;alpha-bromo-4-tolunitrile;4-bromomethyl benzonitrile;alpha-bromo-p-cyanotoluene;SCHEMBL531;alpha-bromo-4-toluonitrile;NCIOpen2_001738;UNII-RV332B84ZG;1-bromomethyl-4-cyanobenzene;4-(bromo-methyl)benzonitrile;4-(bromomethyl)-benzonitrile;(4-cyanophenyl)methyl bromide;4-(bromo-methyl)-benzonitrile;Benzonitrilo, 4-(bromometil)-;DTXSID40864744;4-(Bromomethyl)benzonitrile, 99%;BCP22608;NSC95792;STL168878;AKOS000268730;AC-8256;CS-W001931;GS-3163;BP-21342;AM20060010;BB 0259257;C1398;FT-0622123;EN300-17712;10.14272/UMLFTCYAQPPZER-UHFFFAOYSA-N;A25002;A905245;doi:10.14272/UMLFTCYAQPPZER-UHFFFAOYSA-N.1;Q-200404;Z56995138;4-(Bromomethyl)benzonitrile, purum, >=95.0% (HPLC)

Chemical Property of 4-Cyanobenzyl bromide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00321mmHg at 25°C
• Melting Point: 113-117 ºC
• Refractive Index: 1.588
• Boiling Point: 283.2 ºC at 760 mmHg
• Flash Point: 125.1 ºC
• PSA: 23.79000
• Density: 1.51 g/cm³
• LogP: 2.45318
• Storage Temp.: Store at 0-5°C
• Water Solubility.: Soluble in chloroform and methanol. Insoluble in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 194.96836
• Heavy Atom Count: 10
• Complexity: 139

Purity/Quality:

98% ^*data from raw suppliers

4-Cyanobenzyl Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-42/43
• Safety Statements: 22-26-36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CBr)C#N
• Uses: 4-Cyanobenzyl bromide is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine. A benzyl halide as postemergence herbicides. 4-(Bromomethyl)benzonitrile is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide. 4-(Bromomethyl)benzonitrile may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.

Technology Process of 4-Cyanobenzyl bromide

There total 10 articles about 4-Cyanobenzyl bromide 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%

para-methylbenzonitrile (104-85-8) → 4-cyanobenzyl bromide (17201-43-3)

Guidance literature:

With dihydrogen peroxide; bromine; In dichloromethane; water; for 4h; Reagent/catalyst; Reflux;

Reference yield: 92.0%

para-methylbenzonitrile (104-85-8) + dibenzoyl peroxide (94-36-0) → 4-cyanobenzyl bromide (17201-43-3)

Guidance literature:

With N-Bromosuccinimide; In chloroform; for 24h; Reflux;

DOI:10.1055/s-0033-1339124

Reference yield: 89.0%

4-Cyanobenzyl alcohol (874-89-5) → 4-cyanobenzyl bromide (17201-43-3)

Guidance literature:

With phosphorus pentoxide; potassium bromide; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2015.11.078

upstream raw materials:

para-methylbenzonitrile

bromine

4-cyanobenzaldehyde

para-bromotoluene

Downstream raw materials:

1-(4'-cyanobenzyl)pyridinium bromide

4-((phenylthio)methyl)benzonitrile

4-cyanobenzaldehyde

2,3-bis-(4-cyano-phenyl)-propionitrile

Refernces

• 1、 Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip. "[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization". supporting information. p. 890 - 895. Retrieved 2021/02/01.
• 2、 Zhao, Mengdi,Li, Meiqi,Lu, Wenjun. "Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature". supporting information. p. 4933 - 4939. Retrieved 2018/12/14.