Introduction
3-Bromoaniline, also referred to as m-Bromoaniline, is a
crucial organic compound that finds extensive use across various sectors in
chemistry and industry. This blog post will examine its chemical properties,
methods of synthesis, applications, and safety considerations, emphasizing its
significance in both research and commercial contexts.
Chemical
Properties
- Chemical Name:3-Bromoaniline
- CAS Number:591-19-5
- Molecular Formula:C₆H₆BrN
- Molecular Weight:172.02 g/mol
- Appearance:Off-white to light brown crystalline solid
- Melting Point:31-33°C
- Boiling Point:236-238°C
- Solubility:Slightly soluble in water; soluble in organic solvents such as ethanol,
ether, and chloroform.
The structure of 3-Bromoaniline features a
benzene ring with a bromine atom at the meta position and an amino group at the
para position. This specific arrangement gives 3-Bromoaniline distinctive
chemical reactivity, making it valuable for various chemical transformations.
Related
Products
·
Trifluoromethanesulfonic
acid
Synthesis
3-Bromoaniline is typically synthesized
through the bromination of aniline, followed by purification to isolate the
desired product. Here are two common synthetic routes:
Nitration
and Reduction
- Aniline is first nitrated to produce 3-nitroaniline, achieved by
treating aniline with a mixture of concentrated nitric and sulfuric acids.
- The resultant 3-nitroaniline is then reduced using a suitable
reducing agent, like iron powder combined with hydrochloric acid, to yield
3-bromoaniline.
Direct
Bromination
Alternatively, direct bromination of aniline
can be performed using bromine or a brominating agent such as
N-bromosuccinimide (NBS). Careful control of the reaction conditions ensures
that 3-bromoaniline is the primary product.
Applications
3-Bromoaniline is a versatile compound with
numerous applications, including:
Organic
Synthesis Intermediate
It acts as a key intermediate in synthesizing
various organic compounds, including dyes, pigments, and agrochemicals. The presence of bromine and amino functional
groups facilitates further chemical modifications.
Pharmaceuticals
In the pharmaceutical industry, 3-bromoaniline
serves as a building block for creating active pharmaceutical ingredients
(APIs). It is integral in synthesizing several drugs, including
anti-inflammatory and anticancer agents.
Materials
Science
This compound is utilized in producing
specialty polymers and materials. Its reactivity allows for the incorporation
of functional groups essential for achieving desired material properties.
Research
Reagent
In both academic and industrial research
settings, 3-bromoaniline is employed as a reagent for studying reaction
mechanisms, developing new synthetic methodologies, and exploring chemical
reactivity.
Safety and
Handling
While 3-Bromoaniline is a valuable compound,
it must be handled with caution due to potential hazards:
- Toxicity:Harmful if ingested, inhaled, or
absorbed through the skin. It can irritate the eyes, skin, and respiratory
system.
- Carcinogenicity:Prolonged exposure may have carcinogenic effects, necessitating careful
handling.
- Protective Measures:Always wear personal protective equipment (PPE) such as gloves, goggles,
and lab coats when working with this compound. Conduct experiments in a
well-ventilated area or a fume hood to minimize exposure to vapors and
dust.
- Storage:Store 3-Bromoaniline in a cool, dry
place, away from light and moisture. Ensure that containers are tightly
sealed to prevent contamination and degradation.
Conclusion
