2-Cyanobenzyl bromide
[CAS# 22115-41-9]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 2-Cyanobenzyl bromide
• Synonyms: 2-(Bromomethyl)benzonitrile; alpha-Bromo-o-tolunitrile
• Molecular Formula: C₈H₆BrN
• Molecular Weight: 196.05
• CAS Registry Number: 22115-41-9
• EC Number: 628-473-4
• SMILES: C1=CC=C(C(=C1)CBr)C#N

Properties

• Melting point: 70-74 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314
• Safety Statements: P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301

• Transport Information: UN 3261

Discovery and Applications

2-Cyanobenzyl bromide, an organic compound with the formula C8H6BrN, was first synthesized in the early 20th century during the exploration of benzyl derivatives and halogenated aromatic compounds. The discovery process typically involved bromination of 2-cyanotoluene, where the presence of the nitrile group (–CN) on the benzene ring facilitated selective bromination at the benzylic position.

2-Cyanobenzyl bromide is an important reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-nitrogen bonds. It is used as an alkylating agent to introduce the 2-cyanobenzyl group into various nucleophiles, such as amines, alcohols, and thiols. The presence of both bromine and nitrile functionalities allows for subsequent chemical transformations, making it a versatile intermediate in multi-step synthesis.

In the pharmaceutical industry, 2-cyanobenzyl bromide is used as a key building block in the synthesis of active pharmaceutical ingredients (APIs). It is involved in the production of various drugs, including those with anticancer, antiviral, and antibacterial properties. The compound's reactivity enables the formation of heterocyclic structures and other pharmacophores essential for biological activity.

2-Cyanobenzyl bromide is utilized in the development of advanced materials, particularly in the synthesis of polymers and organic electronic materials. Its ability to form stable covalent bonds with different monomers makes it useful in creating polymers with specific properties, such as enhanced thermal stability and conductivity.

In agriculture, 2-cyanobenzyl bromide serves as an intermediate in the synthesis of herbicides, insecticides, and fungicides. Its derivatives help in protecting crops from pests and diseases.

Academic and industrial researchers use 2-cyanobenzyl bromide to explore new chemical reactions and mechanisms. Its well-defined reactivity provides a model for studying substitution reactions and the behavior of nitrile-containing compounds.

In biochemical research, 2-cyanobenzyl bromide is used to study enzyme inhibition and protein modification. It can selectively modify amino acids in proteins, helping researchers understand protein structure and function.

References

2001. Crystal structure of 25,27-bis[(2-cyanophenyl)methoxy] calix[4]arene. Journal of Chemical Crystallography, 31(6).
DOI: 10.1023/a:1014355506343

2008. 1-(3-Amino-1H-inden-2-yl)ethanone. Acta Crystallographica. Section E, Structure Reports Online, 64(11).
DOI: 10.1107/s1600536808033485

2011. 1,3-Bis(2-cyano-benz-yl)imidazolium bromide. Acta Crystallographica. Section E, Structure Reports Online, 67(12).
DOI: 10.1107/s1600536811048951