4-Bromomethylbenzoic acid
[CAS# 6232-88-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 4-Bromomethylbenzoic acid
• Synonyms: alpha-Bromo-p-toluic acid
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.05
• CAS Registry Number: 6232-88-8
• EC Number: 228-343-3
• SMILES: C1=CC(=CC=C1CBr)C(=O)O

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 223-227 °C
• Index of Refraction: 1.614, Calc.^*
• Boiling Point: 328.8±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 152.7±23.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H314-H315-H319-H335
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P308+P316-P316-P317-P319-P320-P321-P333+P317-P362+P364-P363-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
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

4-Bromomethylbenzoic acid, a derivative of benzoic acid, is an organic compound with the chemical formula C9H9BrO2. Its structure features a bromomethyl group attached to the para position of the benzoic acid moiety, giving it unique properties and potential applications in various fields, including organic synthesis and materials science.

The discovery of 4-bromomethylbenzoic acid can be traced back to the systematic study of substituted benzoic acids in the mid-20th century. The compound is synthesized through various methods, with one common approach involving the bromination of methylbenzoic acid derivatives, specifically in the presence of brominating agents such as phosphorus tribromide or N-bromosuccinimide. This process selectively introduces the bromomethyl group, resulting in the formation of 4-bromomethylbenzoic acid.

4-Bromomethylbenzoic acid is notable for its role as a versatile intermediate in organic synthesis. Its unique structure allows it to participate in various chemical reactions, making it valuable in the production of pharmaceuticals, agrochemicals, and polymer materials. One of the primary applications of this compound is in the synthesis of polymer additives and cross-linking agents. For instance, when reacted with amines or alcohols, it can form esters or amides that are useful in modifying polymer properties, such as enhancing thermal stability or mechanical strength.

In addition to its applications in polymer chemistry, 4-bromomethylbenzoic acid has been explored for its potential as a reagent in medicinal chemistry. Its ability to introduce the bromomethyl group into various molecular frameworks allows for the design of novel bioactive compounds. Researchers have investigated its use in the synthesis of pharmaceuticals, including potential anticancer agents and antimicrobial drugs. The bromomethyl moiety can serve as a leaving group or a site for further functionalization, enabling the development of more complex structures with targeted biological activity.

Moreover, 4-bromomethylbenzoic acid has applications in the field of materials science, particularly in the synthesis of functionalized materials. Its reactivity facilitates the incorporation of the bromomethyl group into various substrates, allowing for the development of materials with enhanced properties, such as improved adhesion, solubility, and processability. This has implications in industries ranging from coatings to adhesives and sealants.

Despite its diverse applications, safety considerations are essential when handling 4-bromomethylbenzoic acid. As a brominated compound, it may pose certain health risks, including potential irritation to the skin and eyes. Proper laboratory practices, including the use of personal protective equipment and adherence to safety guidelines, are crucial to mitigate these risks.

In summary, 4-bromomethylbenzoic acid is an important compound with a rich history of discovery and a wide range of applications in organic synthesis, medicinal chemistry, and materials science. Its unique structural features and reactivity continue to make it a subject of interest in scientific research, highlighting its relevance across multiple disciplines.

References

2008. Airborne allergic contact dermatitis from 4-(bromomethyl)benzoic acid in a university chemist. Contact Dermatitis, 58(4).
DOI: 10.1111/j.1600-0536.2007.01293.x

2011. {8-[4-(Bromo-meth-yl)benzo-yl]-2,7-dimeth-oxy-naphthalen-1-yl}[4-(bromo-meth-yl)phen-yl]methanone. Acta Crystallographica. Section E, Structure Reports Online, 67(8).
DOI: 10.1107/s1600536811029151

2011. Airborne contact dermatitis - current perspectives in etiopathogenesis and management. Indian Journal of Dermatology, 56(6).
DOI: 10.4103/0019-5154.91832