2-Bromo-4-fluoroaniline
[CAS# 1003-98-1]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoroaniline series
• Name: 2-Bromo-4-fluoroaniline
• Molecular Formula: C₆H₅BrFN
• Molecular Weight: 190.01
• CAS Registry Number: 1003-98-1
• EC Number: 619-469-3
• SMILES: C1=CC(=C(C=C1F)Br)N

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*, 1.67 g/mL (Expl.)
• Index of Refraction: 1.597, Calc.^*, 1.583 (Expl.)
• Boiling Point: 221.0±0.0 °C (760 mmHg), Calc.^*, 221 °C (Expl.)
• Flash Point: 104.4±0.0 °C, Calc.^*, 104 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-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
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Bromo-4-fluoroaniline is an organohalide compound with significant applications in pharmaceuticals, agrochemicals, and material science. Its molecular structure, characterized by an aniline group substituted with bromine and fluorine atoms on a benzene ring, makes it a versatile building block in organic synthesis. The compound's discovery and development are closely linked to the growing demand for halogenated aromatics in fine chemical production.

The synthesis of 2-bromo-4-fluoroaniline often involves selective halogenation and amination reactions. A common method includes the controlled bromination of 4-fluoroaniline under specific conditions to ensure regioselectivity. The presence of electron-withdrawing and donating groups facilitates subsequent transformations, making the compound highly adaptable for various chemical modifications.

In the pharmaceutical industry, 2-bromo-4-fluoroaniline is an important intermediate in the synthesis of active pharmaceutical ingredients (APIs). Its halogenated structure provides opportunities for introducing additional functional groups, allowing chemists to design complex molecules with desired biological properties. This compound has been utilized in the development of drugs targeting diseases such as cancer and infectious conditions, where the fluorine atom enhances metabolic stability and the bromine atom facilitates diverse coupling reactions.

The agrochemical sector also benefits from 2-bromo-4-fluoroaniline as a precursor for herbicides and pesticides. Halogenated anilines are known for their ability to disrupt specific biochemical pathways in plants and pests, making them effective in crop protection products. The unique substitution pattern of this compound contributes to the specificity and potency of the resulting agrochemicals.

Beyond its role in pharmaceuticals and agrochemicals, 2-bromo-4-fluoroaniline is used in materials science for the preparation of functionalized polymers and dyes. The compound’s reactivity enables its incorporation into complex polymer backbones, enhancing properties like thermal stability and chemical resistance. In dye production, its structure allows for vivid and durable colorant formulations used in textiles and coatings.

Recent research has focused on optimizing the production and utilization of 2-bromo-4-fluoroaniline. Efforts include developing greener synthesis routes that minimize waste and exploring its potential in novel applications such as organic electronics. These advancements underscore the compound’s enduring relevance in modern chemistry.

References

2010. Synthesis from 2-Bromoanilines and Carboxylic Acid Chlorides. Science of Synthesis.
URL: SD-111-00444

2015. Synthesis and biological evaluation of novel laropiprant derivatives as potential anti-allergic agents. Medicinal Chemistry Research, 24(4).
DOI: 10.1007/s00044-015-1431-8

2024. Efficient Synthesis of 8-Fluoro-10-methyl-3,4-dihydrobenzo[b][1,6]naphthyridine-2(1H)-carboxamides and Their Cytotoxic Activity. Russian Journal of Organic Chemistry, 60(9).
DOI: 10.1134/s1070428024090203