2-Bromoethyl benzoate
[CAS# 939-54-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2-Bromoethyl benzoate
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07
• CAS Registry Number: 939-54-8
• EC Number: 628-389-8
• SMILES: C1=CC=C(C=C1)C(=O)OCCBr

Properties

• Density: 1.445
• Boiling point: 157-159 ºC (20 mmHg)
• Refractive index: 1.548
• Flash point: >110 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2-Bromoethyl benzoate is an organic compound consisting of a benzoate ester group attached to a 2-bromoethyl chain. This compound is part of the larger family of bromobenzene derivatives, where the bromoethyl group at the second position of the benzene ring enhances its reactivity and allows for a range of chemical transformations. It is commonly used as a building block in organic synthesis, serving as a precursor to various functionalized compounds.

The discovery and development of 2-bromoethyl benzoate can be traced to standard organic synthesis techniques involving the reaction of ethyl benzoate with bromine or a brominating agent under controlled conditions. The bromoethyl group is introduced onto the benzene ring, specifically at the ortho position relative to the ester group, by an electrophilic substitution mechanism. This results in the formation of 2-bromoethyl benzoate, which is typically isolated in high yield through simple purification steps, such as recrystallization or distillation.

In organic synthesis, 2-bromoethyl benzoate serves as a versatile intermediate for the introduction of various functional groups. The bromoethyl group is highly reactive, enabling nucleophilic substitution reactions, where the bromine atom can be replaced by a range of nucleophiles such as alcohols, amines, or thiols. This makes 2-bromoethyl benzoate an important precursor in the synthesis of more complex molecules, particularly those containing alkyl or aryl functional groups. For example, it can be used to prepare alkylated benzoate derivatives or to introduce heteroatoms into the aromatic ring through various coupling reactions.

In the pharmaceutical industry, 2-bromoethyl benzoate has been explored for its potential as a starting material in the synthesis of biologically active compounds. The ability to modify the ester group or the bromoethyl side chain allows for the generation of a range of derivatives that may exhibit desirable pharmacological properties. Compounds derived from 2-bromoethyl benzoate have been studied for their antimicrobial, anticancer, and anti-inflammatory activities. The structural versatility of the molecule makes it a valuable scaffold for medicinal chemists seeking to design novel therapeutic agents.

In addition to its role in pharmaceutical synthesis, 2-bromoethyl benzoate has applications in materials science, particularly in the development of functionalized polymers and materials with specific electronic or optical properties. The reactive bromoethyl group can be used to polymerize with other monomers to produce copolymers, which may exhibit unique characteristics for use in coatings, adhesives, and electronic devices. Moreover, the introduction of the bromoethyl group at the ortho position relative to the ester group allows for controlled reactivity, enabling the selective functionalization of the aromatic ring in a variety of synthetic pathways.

Another notable application of 2-bromoethyl benzoate is in the field of chemical biology. The compound can be utilized as a probe or linker in biochemical research, allowing for the study of protein-ligand interactions or the attachment of biomolecules to surfaces for various analytical techniques. Its reactivity and ease of modification make it a useful tool in chemical and biological research, particularly in the design of targeted drug delivery systems or the creation of biosensors.

In conclusion, 2-bromoethyl benzoate is a valuable chemical intermediate in both academic research and industrial applications. Its ability to undergo various chemical reactions makes it an essential building block for the synthesis of complex organic molecules, particularly in the pharmaceutical and materials science sectors. As research progresses and new applications are discovered, the importance of 2-bromoethyl benzoate in synthetic chemistry and related fields will likely continue to grow.

References

2011. Cleavage of 2-Haloethyl Esters. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-120-00035