Ethyl 4-bromophenylacetate
[CAS# 14062-25-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: Ethyl 4-bromophenylacetate
• Synonyms: 4-Bromophenylacetic acid ethyl ester
• Molecular Formula: C₁₀H₁₁BrO₂
• Molecular Weight: 243.10
• CAS Registry Number: 14062-25-0
• EC Number: 628-950-7
• SMILES: CCOC(=O)CC1=CC=C(C=C1)Br

Properties

• Melting Point: 29-31 °
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Ethyl 4-bromophenylacetate, an organic compound with the formula C10H11BrO2, was first synthesized in the early 20th century as part of research into brominated aromatic esters. This compound is typically produced through the esterification of 4-bromophenylacetic acid with ethanol, using an acid catalyst. The discovery of ethyl 4-bromophenylacetate provided chemists with a useful intermediate for various organic synthesis applications.

Ethyl 4-bromophenylacetate is widely used as an intermediate in organic synthesis. Its structure, featuring both an ester and a bromine-substituted aromatic ring, makes it highly reactive and suitable for various chemical transformations. It can undergo nucleophilic substitution reactions, where the bromine atom is replaced by different nucleophiles, leading to the synthesis of diverse compounds. Additionally, the ester group can be hydrolyzed to yield 4-bromophenylacetic acid, which can then be further modified.

In the pharmaceutical industry, ethyl 4-bromophenylacetate is used to synthesize active pharmaceutical ingredients (APIs) and intermediates. Its reactivity allows for the introduction of various functional groups necessary for drug development. For instance, it can be used to create compounds with potential anti-inflammatory, analgesic, or anticancer properties.

Ethyl 4-bromophenylacetate is employed in the agrochemical sector to produce herbicides, insecticides, and fungicides. The brominated aromatic ester structure allows for the development of agrochemicals with specific biological activities, targeting particular pests or pathogens while minimizing harm to the crops.

In materials science, ethyl 4-bromophenylacetate is used in the synthesis of polymers and advanced materials. Its reactivity with various monomers can create polymers with unique properties, such as enhanced durability, chemical resistance, and mechanical strength. These materials are used in coatings, adhesives, and high-performance engineering plastics.

Ethyl 4-bromophenylacetate is utilized in academic and industrial research to explore new synthetic methodologies and reaction mechanisms. Researchers use it as a model compound to study substitution reactions, esterification, and other organic processes.

In the flavor and fragrance industry, ethyl 4-bromophenylacetate is used as an intermediate to synthesize aroma compounds. Its derivatives can impart pleasant floral and fruity notes, enhancing the sensory qualities of various products, including perfumes, food additives, and personal care items.

References

2018. On-demand synthesis of organozinc halides under continuous flow conditions. Nature Protocols. Mateo Berton, Lena Huck, Jesús Alcázar.
DOI: 10.1038/nprot.2017.141

2018. C—H Arylation Reactions Using Aryl Halides and Consecutive Photoinduced Electron Transfer (conPET) Catalysts. Science of Synthesis.
DOI: SD-229-00253

2015. Synthesis of Esters. Science of Synthesis.
DOI: SD-218-00126