Ethyl 4-bromobutyrate
[CAS# 2969-81-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl 4-bromobutyrate
• Synonyms: 4-Bromobutyric acid ethyl ester
• Molecular Formula: C₆H₁₁BrO₂
• Molecular Weight: 195.05
• CAS Registry Number: 2969-81-5
• EC Number: 221-005-6
• SMILES: CCOC(=O)CCCBr

Properties

• Density: 1.363
• Boiling point: 80-82 °C (10 mmHg)
• Refractive index: 1.4549-1.4569
• Flash point: 90 °C
• Water solubility: immiscible

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Skin sensitization	Skin Sens.	1	H317
Flammable liquids	Flam. Liq.	3	H226
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 2929

Discovery and Applications

Ethyl 4-bromobutyrate is an organic compound with the formula C6H11BrO2. It was first synthesized in the early 20th century during research into halogenated esters and their potential applications in organic synthesis. This compound is typically produced by the esterification of 4-bromobutyric acid with ethanol, a reaction facilitated by acid catalysts.

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

In the pharmaceutical industry, ethyl 4-bromobutyrate is used to synthesize active pharmaceutical ingredients (APIs) and intermediates. Its reactivity allows for the introduction of various functional groups necessary for the development of drugs. For example, it can be used to create ?-aminobutyric acid (GABA) analogs, which are important in the treatment of neurological disorders such as epilepsy and anxiety.

Ethyl 4-bromobutyrate is employed in the agrochemical sector to produce herbicides, insecticides, and fungicides. The chemical's brominated 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-bromobutyrate is used in the synthesis of polymers and resins. Its reactivity with various monomers can create polymers with unique properties, such as enhanced durability and chemical resistance. These materials are used in coatings, adhesives, and other applications where performance and longevity are critical. The compound's ability to introduce functional groups into polymer chains makes it a useful component in developing advanced materials with specific characteristics.

Ethyl 4-bromobutyrate 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-bromobutyrate is used as an intermediate to synthesize aroma compounds. Its derivatives can impart fruity and floral notes, enhancing the sensory qualities of various products, including perfumes, food additives, and personal care items.

References

2022. Synthesis and Evaluation of New 5,15-Diarylporphyrin Derivatives for Photodynamic Therapy, _Pharmaceutical Chemistry Journal_, 56(7)
DOI: https://doi.org/10.1007/s11094-022-02711-1

1986, Reexamination of the intimate ion pair mechanism in the gas phase pyrolysis kinetics of ethyl 4-bromobutyrate, _Reaction Kinetics, Mechanisms and Catalysis_, 29(1)
DOI: https://doi.org/10.1007/bf02068149

1996, Combinatorial synthesis of small-molecule libraries using 3-amino-5-hydroxybenzoic acid, _Molecular Diversity_, 1(4)
DOI: https://doi.org/10.1007/bf01721326