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:

99% ^*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
• General Description: 4-Cyanobenzyl bromide (also known as p-bromomethylbenzonitrile) serves as a key intermediate in the synthesis of C₃-symmetric s-triazine-based redox-active chromophores. It is used as a starting material to produce a phosphonate-functionalized triazine building block, which can further undergo olefination reactions to form derivatives such as tris(ferrocene)- and tris(tetrathiafulvalene)-triazines. These compounds exhibit redox-active and charge-transfer properties, making them useful in materials chemistry and molecular electronics.

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:

4-((phenylthio)methyl)benzonitrile

p-(diethylaminomethyl)benzonitrile

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

4-cyanobenzaldehyde

Refernces

New building block for C₃ symmetry molecules: Synthesis of s-triazine-based redox active chromophores

10.1021/ol902203t

The research focuses on the synthesis of a novel C3 symmetric building block, a s-triazine-based molecule with three phosphonate groups, which can be easily synthesized in two steps starting from p-bromomethylbenzonitrile. This new building block readily undergoes olefination reactions to yield derivatives such as tris(tetrathiafulvalene)- and tris(ferrocene)-1,3,5-triazines. The experiments involved the preparation of intermediate building block 3 through reactions with triflic anhydride and trimethyl phosphite, followed by olefination reactions with formylferrocene and formylTTF to synthesize the final compounds 5 and 7. The reactants included p-bromomethylbenzonitrile, triflic anhydride, trimethyl phosphite, formylferrocene, and formylTTF. The analyses used to characterize the compounds were spectroscopic techniques (UV-vis, FT-IR, 1H and 13C NMR, HR-MS), cyclic voltammetry for electrochemical characterization, and solvatochromic studies to assess the charge-transfer properties of the synthesized molecules.