2-Amino-5-bromophenol
[CAS# 38191-34-3]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Phenols, ethers and epoxides >> Phenolic flavors
• Name: 2-Amino-5-bromophenol
• Molecular Formula: C₆H₆BrNO
• Molecular Weight: 188.02
• CAS Registry Number: 38191-34-3
• EC Number: 640-282-8
• SMILES: C1=CC(=C(C=C1Br)O)N

Properties

• Melting point: 146-147 $degree
• Boiling point: 265 $degree (760mmHG)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H315-H319-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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-5-bromophenol is a chemical compound with the molecular formula C6H6BrNO, characterized by a bromine atom and an amino group attached to the benzene ring at the 5-position and 2-position, respectively. This compound is a halogenated phenol that has attracted attention from various fields due to its diverse chemical properties and potential applications.

The discovery of 2-amino-5-bromophenol can be traced back to the broader study of halogenated aromatic compounds. Halogenation is the process of introducing halogen atoms into organic molecules, which can significantly alter their chemical and physical properties, enhancing reactivity, stability, and biological activity. The synthesis of 2-amino-5-bromophenol involves the bromination of 2-aminophenol, a simple process that highlights the accessibility of this compound and its potential for various applications.

One of the major applications of 2-amino-5-bromophenol is in the pharmaceutical field. The compound is an important intermediate in the synthesis of various drugs and bioactive molecules. Its structure enables it to participate in a variety of chemical reactions, helping to produce complex molecules with therapeutic potential. Researchers have explored its use in the development of anti-inflammatory, antibacterial, and anticancer drugs. The presence of both amino and bromine atoms in the molecule provides unique opportunities for designing compounds with enhanced biological activity and specificity.

In the field of organic synthesis, 2-amino-5-bromophenol is valued for its versatility as a building block. It can undergo a variety of reactions, including coupling reactions, nucleophilic substitution, and electrophilic aromatic substitution. These reactions enable the synthesis of a wide range of derivatives, making 2-amino-5-bromophenol a key ingredient in the development of new materials, dyes, and polymers. Its ability to form stable bonds with a variety of functional groups enhances its usefulness in creating complex organic structures.

In addition, 2-amino-5-bromophenol has applications in the field of agrochemicals. It is used in the synthesis of herbicides, fungicides, and insecticides. The bromine atom in the molecule can improve the efficacy and stability of these agrochemicals, ensuring effective control of pests and weeds. The role of this compound as a synthetic intermediate in the production of agrochemicals highlights its importance in supporting modern agricultural practices and increasing crop yields.

This compound is also used in the dye and pigment industry. Its ability to form bright and stable colors is suitable for the production of dyes and pigments for textiles, inks, and coatings. Introducing halogen atoms such as bromine into dye molecules can enhance the colorfastness and resistance to environmental factors of dyes, making them more durable and long-lasting.

Due to its chemical reactivity, careful consideration is required when handling and storing 2-amino-5-bromophenol. It should be stored in a cool, dry place away from incompatible materials. Appropriate safety precautions, including the use of gloves, goggles, and adequate ventilation, are essential to prevent exposure and ensure safe handling. Proper disposal methods should be followed to minimize environmental impact.

References

2021. One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies. Russian Journal of Bioorganic Chemistry, 47(6).
DOI: 10.1134/s1068162021060091

2020. Synthesis, anticancer evaluation, and molecular docking studies of benzoxazole linked combretastatin analogues. Medicinal Chemistry Research, 29(3).
DOI: 10.1007/s00044-020-02504-9

2015. A Facile Synthesis of 2-Aminobenzoxazoles and 2-Aminobenzimidazoles Using N-Cyano-N-phenyl-p-toluenesulfonamide (NCTS) as an Efficient Electrophilic Cyanating Agent. Synlett, 26(9).
DOI: 10.1055/s-0034-1380166