General Description

2-Bromo-5-chloronitrobenzene is a valuable chemical compound with unique properties that make it useful in various applications. It possesses a high melting point and is sparingly soluble in water but soluble in organic solvents. Its reactivity makes it an important building block in organic synthesis and a valuable intermediate in the production of pharmaceuticals, agrochemicals, and dyes. Additionally, its ability to enhance electron-donating ability and improve conductivity makes it useful in the fabrication of organic electronic devices. However, handling this compound requires caution due to its potential to cause skin, eye, and respiratory irritation. Overall, 2-Bromo-5-chloronitrobenzene serves as a versatile compound with diverse opportunities for research and industrial applications.

Figure 1. 2-Bromo-5-chloronitrobenzene

Properties

2-Bromo-5-chloronitrobenzene is a chemical compound with distinctive properties. It is a pale yellow crystalline solid with a molecular formula of C6H3BrClNO2 and a molecular weight of 236.45 g/mol. This compound possesses a high melting point of approximately 82-86°C and is sparingly soluble in water, but soluble in organic solvents such as acetone and ethanol. One of the notable features of 2-Bromo-5-chloronitrobenzene is its reactivity, particularly in substitution reactions due to the presence of both bromine and chlorine atoms on the benzene ring. It serves as a valuable intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes. Additionally, its unique combination of functional groups makes it an important building block in organic synthesis. Furthermore, 2-Bromo-5-chloronitrobenzene exhibits potential for use as a precursor in the preparation of materials for electronic and optical applications. Its properties make it a subject of interest in the field of materials science and organic chemistry, offering diverse opportunities for further research and industrial applications. ¹

Applications

2-Bromo-5-chloronitrobenzene, also known as Bromochloronitrobenzene, is a chemical compound that finds various applications in organic synthesis and pharmaceutical research. Its unique chemical properties make it a valuable reagent in several important processes. One of the key applications of 2-Bromo-5-chloronitrobenzene is in the synthesis of indole derivatives. Indole derivatives are essential building blocks in the production of pharmaceutical drugs and natural products. By reacting with suitable reagents, 2-Bromo-5-chloronitrobenzene can be used to synthesize diindolylmethane, which exhibits potential anti-cancer properties. Another significant application of 2-Bromo-5-chloronitrobenzene lies in organic electronics, particularly in the synthesis of ladder-type oligomers like polyaniline. These oligomers possess excellent electrical conductivity and are used in the fabrication of organic electronic devices, such as light-emitting diodes (LEDs), solar cells, and field-effect transistors. The presence of bromine and chlorine atoms in the compound enhances its electron-donating ability and improves the conductivity of the resulting oligomer. Furthermore, 2-Bromo-5-chloronitrobenzene is employed in the synthesis of novel benzene sulfonamides, which have shown promising results as cell cycle inhibitors. These compounds have the potential to disrupt the growth and division of cancer cells, making them potential candidates for the development of anti-cancer drugs. In summary, 2-Bromo-5-chloronitrobenzene serves as a versatile intermediate in the synthesis of various compounds with applications in pharmaceutical research and organic electronics. Its role in the production of indole derivatives, ladder-type oligomers, and benzene sulfonamides highlights its significance in advancing these fields. ²

Safety

2-Bromo-5-chloronitrobenzene is a chemical compound commonly used in various industrial processes. It is important to understand the safety considerations associated with this substance. Firstly, 2-Bromo-5-chloronitrobenzene has been identified as a skin irritant. Direct contact with the compound may lead to redness, itching, and inflammation of the skin. Therefore, it is crucial to wear appropriate protective clothing, such as gloves and lab coats, when handling this chemical. Secondly, this compound can cause serious eye irritation. Accidental exposure or splashes may result in pain, tearing, and blurred vision. In case of eye contact, immediate rinsing with water for several minutes is recommended, and medical attention should be sought if symptoms persist. Additionally, 2-Bromo-5-chloronitrobenzene may cause respiratory irritation. Inhalation of its vapors or dust particles can irritate the respiratory system, leading to coughing, shortness of breath, and discomfort. Adequate ventilation and respiratory protective equipment should be used in areas where this compound is present. It is essential to handle 2-Bromo-5-chloronitrobenzene with caution and follow proper safety protocols to minimize the risk of adverse effects. This includes storing the chemical in a well-ventilated area, using it in designated areas with appropriate safety measures, and disposing of it according to regulatory guidelines. ³

Reference

1. PubChem. COMPOUND SUMMARY: 2-Bromo-5-chloronitrobenzene. National Library of Medicine, PubChem CID: 2794904.

2. Other Fused-Ring Hetarylboronic Acids and Derivatives. Science of Synthesis, 2012, 1, 258.

3. 2-Bromo-5-chloronitrobenzene. European Chemicals Agency, EC List no. 255-421-4.