4-Bromobenzoic acid
[CAS# 586-76-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 4-Bromobenzoic acid
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• CAS Registry Number: 586-76-5
• EC Number: 209-581-7
• SMILES: C1=CC(=CC=C1C(=O)O)Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*, 1.894 g/mL (Expl.)
• Melting point: 252-254 °C (Expl.)
• Index of Refraction: 1.608, Calc.^*
• Boiling Point: 299.8±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 135.1±22.6 °C, Calc.^*
• Water solubility: SOLUBLE IN HOT WATER

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

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS09 Danger
• Risk Statements: H302-H311-H315-H319-H331-H332-H335-H400
• Safety Statements: P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

4-Bromobenzoic acid is an organic compound belonging to the class of benzoic acids, characterized by a carboxyl group (-COOH) attached to a benzene ring, with a bromine atom positioned at the para (4) location relative to the carboxyl group. It is widely used as an intermediate in the synthesis of various chemical compounds.

The compound was first synthesized and characterized in the 19th century, and its properties and reactivity have since been well-studied. Its discovery is part of the broader interest in halogenated aromatic compounds, which have been investigated for their unique chemical reactivity, particularly in electrophilic substitution reactions.

4-Bromobenzoic acid is primarily used in the preparation of other chemicals. It serves as a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and materials. The bromine atom at the para position of the benzene ring plays a crucial role in influencing the reactivity and stability of the molecule, allowing it to participate in a variety of chemical reactions, including nucleophilic substitution, electrophilic aromatic substitution, and cross-coupling reactions.

One significant application of 4-bromobenzoic acid is in the preparation of liquid crystal materials. It is used as a precursor in the synthesis of aromatic esters and other compounds that are incorporated into liquid crystal displays (LCDs). These materials are essential for the production of modern electronic devices, such as flat-screen televisions and computer monitors.

In addition to its use in materials science, 4-bromobenzoic acid is also employed in the synthesis of pharmaceuticals. It is used to produce various biologically active compounds, including antibiotics, anti-inflammatory agents, and other therapeutic molecules. The presence of the bromine atom enhances the molecule's ability to undergo specific chemical transformations, making it a valuable building block for drug discovery and development.

Moreover, 4-bromobenzoic acid is used in the synthesis of aromatic polymers, including polyamides and polyesters. These polymers find applications in coatings, adhesives, and engineering plastics. The compound's ability to participate in polymerization reactions makes it an important component in the production of high-performance materials.

4-Bromobenzoic acid is also used in research settings, particularly in the study of chemical reactions and the development of new synthetic methods. Its well-established reactivity patterns and the presence of the carboxyl and bromine functional groups make it an ideal model compound for studying electrophilic aromatic substitution reactions, nucleophilic aromatic substitution, and other types of organic transformations.

In summary, 4-bromobenzoic acid is a versatile and widely used chemical intermediate in various fields, including pharmaceuticals, materials science, and polymer chemistry. Its applications are supported by its well-established reactivity and utility in the synthesis of complex molecules and materials. The compound continues to play an important role in both academic research and industrial applications.

References

1966. An easily constructed design of combustion apparatus for the microdetermination of carbon and hydrogen in organic compounds. Microchimica Acta, 54(11).
DOI: 10.1007/bf01217703

2021. Synthesis, biological evaluation and docking studies of 1,2,4-oxadiazole linked 5-fluorouracil derivatives as anticancer agents. BMC Chemistry, 15(1).
DOI: 10.1186/s13065-021-00757-y

2022. Aerobic Photooxidation of Toluene Derivatives into Carboxylic Acids with Bromine-Water under Catalyst-Free Conditions. Synlett, 33(16).
DOI: 10.1055/a-1887-7885