2-Bromoaniline
[CAS# 615-36-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 2-Bromoaniline
• Synonyms: o-Bromoaniline; 2-Bromobenzenamine
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• CAS Registry Number: 615-36-1
• EC Number: 210-421-3
• SMILES: C1=CC=C(C(=C1)N)Br

Properties

• Density: 1.52 g/mL (Expl.)
• Melting point: 24-28 °C (Expl.)
• Boiling point: 229 °C (Expl.)
• Refractive index: 1.617-1.619 (Expl.)
• Flash point: 110 °C (Expl.)

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H311-H373-H411
• Safety Statements: P260-P262-P264-P270-P273-P280-P301+P317-P302+P352-P316-P319-P321-P330-P361+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2-Bromoaniline, an organic compound belonging to the class of aniline derivatives, is recognized for its significant role in synthetic chemistry and its diverse applications in industries such as pharmaceuticals, agrochemicals, and dyes. The substance is characterized by the presence of a bromine atom attached to the second carbon of the benzene ring in the aniline structure. This halogenated aromatic amine is typically synthesized by halogenating aniline with a brominating agent, a process that introduces the bromine atom to the aromatic ring. The discovery of 2-bromoaniline dates back to the late 19th century, as researchers in organic chemistry began investigating the reactivity of halogenated anilines and their potential uses in various chemical transformations.

The compound's unique structure—comprising a bromine atom and an amine group attached to a benzene ring—makes it highly reactive and useful as an intermediate in several chemical reactions. The position of the bromine atom on the aromatic ring significantly affects the compound's reactivity, particularly in electrophilic aromatic substitution reactions. 2-Bromoaniline can undergo reactions such as nucleophilic substitution, reduction, and coupling reactions, where it acts as a key building block for the synthesis of a wide array of complex molecules.

One of the primary applications of 2-bromoaniline is in the production of pharmaceuticals. The presence of the bromine atom on the aromatic ring enhances the compound's reactivity, enabling it to participate in various chemical transformations that yield bioactive molecules. For example, 2-bromoaniline is used in the synthesis of drugs such as antimicrobial agents, anti-inflammatory compounds, and other therapeutic molecules. The compound's ability to undergo palladium-catalyzed coupling reactions, such as the Suzuki reaction, makes it a valuable intermediate in the synthesis of complex organic molecules with potential medicinal properties.

In the field of agrochemicals, 2-bromoaniline is utilized as a precursor in the synthesis of various herbicides, fungicides, and pesticides. Its reactivity allows it to participate in the creation of molecules that target specific biological processes in plants and pests, providing an essential tool for crop protection. The versatility of 2-bromoaniline in agrochemical synthesis highlights its importance in the development of more efficient and effective chemical treatments for agricultural applications.

The dye industry also benefits from the use of 2-bromoaniline, as it serves as a key intermediate in the production of azo dyes and other colored compounds. Azo dyes, which are widely used in textiles and food coloring, are often synthesized by coupling 2-bromoaniline with various other aromatic compounds. The bromine atom enhances the compound's ability to undergo these coupling reactions, facilitating the creation of a diverse range of brightly colored dyes that have applications in both industrial and consumer products.

Additionally, 2-bromoaniline is employed in the synthesis of specialty chemicals, including catalysts and ligands for metal-catalyzed reactions. The compound’s ability to participate in a variety of reactions, such as nucleophilic substitution and cross-coupling reactions, makes it a useful reagent in the development of new materials and chemical processes.

Despite its numerous applications, the use of 2-bromoaniline requires careful handling due to its toxic and potentially hazardous nature. The compound is known to be harmful if ingested, inhaled, or absorbed through the skin, and proper safety precautions are necessary when working with it in a laboratory or industrial setting. Researchers and manufacturers must adhere to safety guidelines to minimize exposure and ensure the safe use of this chemical substance.

In conclusion, 2-bromoaniline is an important chemical substance with a wide range of applications across industries such as pharmaceuticals, agrochemicals, dyes, and specialty chemicals. Its unique reactivity, particularly in electrophilic aromatic substitution reactions, allows it to be used as a versatile intermediate in the synthesis of complex molecules with significant industrial and medicinal value. Ongoing research into the applications of 2-bromoaniline will likely continue to expand its role in chemical synthesis, contributing to advancements in drug development, agricultural chemistry, and materials science.

References

2022. Silica Supported Acids (SiO2-HClO4, SiO2-KHSO4) as Eco-Friendly Reuasble Catalysts for Bromination of Aromatic and Heteroaromatic Compounds Using KBr under Solvothermal and Solvent-Free Conditions. Silicon.
DOI: 10.1007/s12633-021-01489-3

2022. Synthesis from 2-Bromoanilines, Isocyanides and Alkynes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-01447

2024. Photosensitized Heterolytic Fission of Isomeric Bromoanilines by Using Methylene Blue as Photosensitizer. Russian Journal of General Chemistry.
DOI: 10.1134/s1070363224060240