4-Bromoaniline, also known as p-bromoaniline, is an organic compound that belongs to the class of aromatic amines. Its chemical structure consists of a bromine atom attached to the para position of an aniline ring. The molecular formula for 4-bromoaniline is C₆H₆BrN, and it has a molar mass of 172.02 g/mol.
Chemical Structure and Properties
The structure of 4-bromoaniline features a benzene ring bonded to an amino group (-NH₂) and a bromine atom (Br) at the para position relative to the amino group. This specific substitution pattern significantly influences the compound’s chemical reactivity and physical properties.
- Molecular Formula: C₆H₆BrN
- Molecular Weight: 172.02 g/mol
- Melting Point: 66-70°C
- Boiling Point: 230°C
- Density: 1.626 g/cm³
4-Bromoaniline appears as a white to slightly yellow crystalline solid with a faint, aromatic odor. It is moderately soluble in water but more soluble in organic solvents like ethanol, ether, and chloroform.
Synthesis
The synthesis of 4-bromoaniline can be achieved through several methods, most commonly by the bromination of aniline. This process typically involves the reaction of aniline with bromine in the presence of a mild oxidizing agent, such as sodium acetate, or a catalyst like copper(II) bromide. The reaction is controlled to ensure bromination occurs specifically at the para position due to the activating effect of the amino group.
An alternative synthesis method involves the reduction of 4-nitrobromobenzene. In this process, 4-nitrobromobenzene is reduced using a suitable reducing agent such as iron powder in acidic conditions, which converts the nitro group to an amino group, yielding 4-bromoaniline.
Applications
4-Bromoaniline is an important intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, dyes, and other fine chemicals.
- Pharmaceuticals: It is used as a building block in the synthesis of various pharmaceutical compounds, including analgesics, antihistamines, and antipsychotics. The bromine atom serves as a versatile functional group for further chemical modifications, which can be exploited to optimize the biological activity of drug candidates.
- Agrochemicals: In the agrochemical industry, 4-bromoaniline is utilized in the synthesis of herbicides, fungicides, and insecticides. The bromine substituent enhances the bioactivity and stability of these compounds, making them more effective in protecting crops.
- Dyes and Pigments: 4-Bromoaniline is a precursor in the production of various dyes and pigments. The amino group facilitates the formation of azo dyes, while the bromine atom can influence the color and fastness properties of the dyes.
- Other Fine Chemicals: 4-Bromoaniline is also employed in the synthesis of specialty chemicals used in the rubber and plastics industries. It can act as a stabilizer, antioxidant, or intermediate in the production of more complex chemical entities.
Safety and Handling
Like many aromatic amines, 4-bromoaniline poses certain health risks and must be handled with care. It is a potential irritant to the skin, eyes, and respiratory tract. Prolonged or repeated exposure can lead to more serious health effects, including methemoglobinemia, which impairs the blood’s ability to carry oxygen. Appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats should be worn when handling this chemical.
In case of accidental exposure, immediate first aid measures include flushing the affected area with plenty of water and seeking medical attention. It is also important to work with 4-bromoaniline in a well-ventilated area or under a fume hood to minimize inhalation risks.
Environmental Impact
4-Bromoaniline can pose environmental hazards if not managed properly. It is considered toxic to aquatic life and can cause long-term adverse effects in aquatic environments. Therefore, waste containing 4-bromoaniline should be disposed of following local regulations and environmental guidelines to prevent contamination of water bodies and soil.
Conclusion
4-Bromoaniline is a versatile organic compound with significant applications across various industries, particularly in the production of pharmaceuticals, agrochemicals, and dyes. Despite its usefulness, proper handling and disposal practices are crucial to mitigate its health risks and environmental impact. As research continues, more sustainable and safer methods for synthesizing and utilizing 4-bromoaniline may be developed, further expanding its applications and benefits.nding its properties, safe handling practices, and environmental impact is crucial for professionals working with this compound. As research continues to expand its potential uses, 3-Bromoaniline is expected to remain a valuable asset in modern chemistry.
FAQ
4-Bromoaniline is used as a precursor in the production of azo dyes and dihydroquinazolines..
4-Bromoaniline can be made by reacting acetyl chloride-protected aniline with bromine.
3-BROMOANILINE Structure – C6H6BrN – Over 100 million chemical compounds | CCDDS.
Bromocriptine is in a class of medications called dopamine receptor agonists. It treats hyperprolactinemia by decreasing the amount of prolactin in the body.
