4-Bromoaniline
[CAS# 106-40-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 4-Bromoaniline
• Synonyms: 4-Bromobenzenamine; p-bromophenylamine
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• CAS Registry Number: 106-40-1
• EC Number: 203-393-9
• SMILES: C1=CC(=CC=C1N)Br

Properties

• Density: 1.5
• Melting point: 60-64 °C
• Boilng point: 222-224 °C
• Water solubility: <0.1 g/100 mL at 23 °C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H302-H311-H315-H319-H332-H335-H373
• Safety Statements: P260-P261-P262-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H331
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

4-Bromoaniline, a derivative of aniline, was first synthesized in the late 19th century by German chemists. The process involved the bromination of aniline, resulting in the substitution of a hydrogen atom with a bromine atom at the para position of the benzene ring. This discovery marked a significant advancement in organic synthesis, expanding the range of available chemical compounds for further study and application. 4-Bromoaniline's distinct chemical structure and properties have since led to its utilization in various industrial and scientific endeavors.

4-Bromoaniline serves as a crucial intermediate in the synthesis of pharmaceutical compounds. It undergoes various chemical reactions to produce pharmaceuticals with diverse therapeutic properties. These compounds include analgesics, antibiotics, and antifungal agents, among others. The versatility of 4-Bromoaniline in pharmaceutical synthesis contributes to the development of new drugs and treatments for various medical conditions.

4-Bromoaniline is utilized in the manufacturing of agrochemicals, particularly herbicides and fungicides. It serves as a building block in the synthesis of active ingredients that control weed growth and fungal infections in crops. By inhibiting the growth of unwanted vegetation and pathogens, agrochemicals containing 4-Bromoaniline contribute to higher crop yields and improved agricultural productivity.

In the dye industry, 4-Bromoaniline acts as an important intermediate in the production of various dyes and pigments. It undergoes diazotization and coupling reactions to form azo dyes, which impart vibrant colors to textiles, plastics, and other materials. The versatility of 4-Bromoaniline in dye synthesis enables the creation of a wide range of colors and shades for diverse applications in the textile and printing industries.

4-Bromoaniline is employed in polymer chemistry as a monomer or polymerization initiator for the synthesis of functional polymers. It participates in polymerization reactions to form polymeric materials with specific properties and applications. These polymers find use in coatings, adhesives, and electronic materials, among other industrial applications, where their chemical and mechanical properties are beneficial.

4-Bromoaniline is utilized in research and development laboratories as a chemical reagent and building block for the synthesis of new compounds. Its availability and reactivity make it a valuable tool for exploring novel chemical structures and properties. Researchers use 4-Bromoaniline to investigate reaction mechanisms, develop new synthetic methodologies, and study the behavior of organic molecules in various environments.

References

2024. Photosensitized Heterolytic Fission of Isomeric Bromoanilines by Using Methylene Blue as Photosensitizer. Russian Journal of General Chemistry, 94(6), 1496-1502.
DOI: 10.1134/s1070363224060240

2024. Selenium species-catalyzed biomimetic halogenations of aromatic and heteroaromatic compounds. Chemical Papers, 78(11), 6957-6968.
DOI: 10.1007/s11696-024-03579-z

1888. Beiträge zur Kenntniss der Azoverbindungen. Monatshefte für Chemie, 9(1), 1109-1127.
DOI: 10.1007/bf01510022