Methyl 4-bromobutyrate
[CAS# 4897-84-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl 4-bromobutyrate
• Synonyms: 4-Bromobutyric acid methyl ester
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• CAS Registry Number: 4897-84-1
• EC Number: 225-523-3
• SMILES: COC(=O)CCCBr

Properties

• Density: 1.434
• Boiling point: 186-187 °C
• Water solubility: insoluble

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
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Methyl 4-bromobutyrate is an organic compound with the formula C5H9BrO2. It was first synthesized in the early 20th century during studies on halogenated esters and their potential applications in organic chemistry. The compound is typically produced by the esterification of 4-bromobutyric acid with methanol, a reaction facilitated by acid catalysts. The discovery of methyl 4-bromobutyrate opened up new avenues for the synthesis of complex organic molecules, providing a versatile intermediate for various chemical reactions.

Methyl 4-bromobutyrate is a crucial intermediate in organic synthesis. Its structure, featuring both an ester and a bromoalkyl group, 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, allowing the synthesis of a wide range of compounds. The ester group can also be hydrolyzed to produce 4-bromobutyric acid, which is used in further chemical syntheses.

In the pharmaceutical industry, methyl 4-bromobutyrate is used to synthesize active pharmaceutical ingredients (APIs) and intermediates. Its reactivity allows for the creation of molecules with specific functional groups necessary for drug development. For example, it can be converted into ?-aminobutyric acid (GABA) analogs, which are important in the treatment of neurological disorders such as epilepsy and anxiety.

Methyl 4-bromobutyrate is employed in the agrochemical sector to produce herbicides, insecticides, and fungicides. The compound'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, methyl 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 properties.

Methyl 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, methyl 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

2024. Design, synthesis and investigating the in vitro and in silico HDAC8 inhibitory activities of derivatives of [6]-shogaol and [6]-gingerol isolated from ginger (Zingiber officinale). Medicinal Chemistry Research.
DOI: 10.1007/s00044-024-03337-6

2023. Design, synthesis and anti-breast cancer properties of butyric ester tethered dihydroartemisinin-isatin hybrids. Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents.
DOI: PMC9926453

2008. Methyl 4-[5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-imidazol-2-ylsulfanyl]butanoate. Acta crystallographica. Section E, Structure reports online.
DOI: PMC2961725