57381-44-9

Basic information

• Product Name: 5-Bromo-2-chlorobenzonitrile
• Synonyms: 5-BROMO-2-CHLOROBENZONITRILE;Benzonitrile,5-broMo-2-chloro-;1-Bromo-4-chloro-3-cyanobenzene;5-BroMo-2-chlorobenzonitrile, 97+%
• CAS NO: 57381-44-9
• Molecular Formula: C₇H₃BrClN
• Molecular Weight: 216.46
• Product Categories: Aromatic Nitriles;Nitrile;Bromine Compounds;Chlorine Compounds;Benzenes
• Mol File: 57381-44-9.mol

Chemical Properties

• Melting Point: 133 °C
• Boiling Point: 266.9 °C at 760 mmHg
• Flash Point: 115.2 °C
• Appearance: /
• Density: 1.74 g/cm³
• Vapor Pressure: 0.00841mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 5-Bromo-2-chlorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-chlorobenzonitrile(57381-44-9)
• EPA Substance Registry System: 5-Bromo-2-chlorobenzonitrile(57381-44-9)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 57381-44-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-chlorobenzonitrile is used as a key intermediate in the synthesis of novel thiazolidin-4-ones, which serve as HIV-1 fusion inhibitors targeting the gp41 protein. These compounds have the potential to disrupt the fusion process of the virus with host cells, thereby inhibiting the replication of HIV-1 and providing a therapeutic approach to combat the disease.
Additionally, 5-Bromo-2-chlorobenzonitrile is utilized in the synthesis of diazinones, which are considered as P2 replacements for pyrazole-based cathepsin S inhibitors. Cathepsin S is a lysosomal cysteine protease enzyme that plays a crucial role in the activation of immune cells and the degradation of proteins. Inhibiting cathepsin S has been explored as a potential therapeutic strategy for various diseases, including cancer and autoimmune disorders.

InChI:InChI=1/C7H3BrClN/c8-6-1-2-7(9)5(3-6)4-10/h1-3H

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 6952-59-6 3-cyanobromobenzene 

Downstream Products

• 1096296-85-3 (5-bromo-2-chloro-phenyl)methanamine 
• 1286670-38-9 5-((5-(4-chloro-3-(1H-tetrazol-5-yl)phenyl)furan-2-yl)methylene)-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-4-one 
• 1262519-03-8 5-(5-bromo-2-chlorophenyl)-1H-tetrazole 
• 1262519-12-9 5-(4-chloro-3-(1H-tetrazol-5-yl)phenyl)furan-2-carbaldehyde 
• 1308649-79-7 ethyl 3-amino-5-bromobenzo[b]thiophene-2-carboxylate 
• 45859-82-3 5-bromobenzo[b]thiophen-3-amine 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 742100-11-4 5-bromo-2-(1H-pyrazol-1-yl)benzonitrile 

Relevant articles and documents

Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles

The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.

Preparation method 5 - bromo -2 -chlorobenzoic acid

The invention provides a preparation method of 5 -bromo -2 -chlorobenzoic acid, which comprises (1) contacting 2 - chlorobenzonitrile with a bromination reagent for bromination reaction to obtain 5 - bromo -2 - chlorobenzonitrile. (2) Hydrolysis of 5 - bromo -2 - chlorobenzonitrile in the presence of a base to give 5 - bromo -2 -chlorobenzoate. The 5 - bromo -2 -chlorobenzoate is then contacted with a protic acid to give 5 - bromo -2 -chlorobenzoic acid. The preparation method has the advantages of simple process, high safety, cheap and accessible raw materials, low cost and 5 - bromo -2 - chlorobenzoic acid yield, high purity and the like.