142356-67-0

Basic information

• Product Name: 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole
• Synonyms: 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole
• CAS NO: 142356-67-0
• Molecular Formula: C7H3Br2ClN2
• Molecular Weight: 310
• Mol File: 142356-67-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole(142356-67-0)
• EPA Substance Registry System: 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole(142356-67-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 142356-67-0(Hazardous Substances Data)

Usage

General Description

5,6-Dibromo-2-chloro-1H-1,3-benzodiazole is a chemical compound with the molecular formula C7H3Br2ClN2. It is a benzodiazole derivative that contains two bromine atoms and one chlorine atom. 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole is primarily used as a building block in organic synthesis and pharmaceutical research. It may also have potential applications in the development of new drugs and agrochemicals. Its properties and reactivity make it a valuable tool for researchers in the study of benzodiazole chemistry and its biological activities.

Upstream product

• 4857-06-1 2-chloro-1H-benzoimidazole 

Relevant articles and documents

Molecular modeling, synthesis, antibacterial and cytotoxicity evaluation of sulfonamide derivatives of benzimidazole, indazole, benzothiazole and thiazole

A new series of heterocyclic molecules bearing sulfonamide linkage has been synthesized and screened for antibacterial activity. During antibacterial screening using broath dilution method, molecules were found to be highly active (MIC value 50–3.1 μg/mL)

Design, synthesis, and antiviral evaluation of 2-chloro-5,6-dihalo-1- β-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections

2-Chloro-5,6-difluorobenzimidazole (8) was prepared from 4,5-difluoro- 2-nitroaniline (5) via successive reduction, cyclization, and diazotization reactions. 2-Chloro-5,6-dibromobenzimidazole (10) was obtained by a direct bromination of 2-chlorobenzimidazole (9) with bromine-water. 2-Chloro-5,6- diiodobenzimidazele (15) was synthesized by a stepwise transformation of the nitre functions of 2-chloro-5,6-dinitrobenzimidazole (11) into iodo groups via diazotization reactions. Ribosylation of 8, 10, and 15 gave the respective β nucleosides 16a-c as the major products along with a small amount of the α anomers 17a-c. Deprotection of 16a-c afforded the corresponding free β nucleosides 2-chloro-5,6-difluoro-1-β-D- ribofuranosylbenzimidazole (2), 2-chloro-5,6-dibromo-1-β-D- ribofuranosylbenzimidazole (3), and 2-chloro-5,6-diiodo-1-β-D- ribofuranosylbenzimidazole (4). Similar deprotection of the α anomers (17a- c) resulted in a removal of the acetyl protecting groups and a concomitant cyclization to give the 2,2'-O-cyclonucleosides (18a-c). Mast of the benzimidazole heterocycles, but not the difluoro analog, were active against human cytomegalovirus (HCMV) (IC50's = 3-40 μM) and herpes simplex virus type 1 (HSV-1) (IC50's = 50-90 μM). This activity, however, was not well separated from cytotoxicity, IC50's = 10-100 μM. The corresponding unsubstituted, the 5,6-dimethyl, and the 5,6-difluoro ribonucleosides (19, 20, and 2, respectively), were inactive against both viruses. Similar to the previously reported 2,5,6-trichloro analog (TCRB), the 5,6-dibromo ribonucleoside 3 was active against HCMV (IC50 ? 4 μM) but more cytotoxic than TCRB. The 5,6-diiodo analog 4 also was active (IC50 ? 2 μM) but more cytotoxic (IC50 = 10-20 μM) than either 3 or TCRB. The cyclonucleosides were inactive against both viruses and not cytotoxic, or slightly active with corresponding cytotoxicity. The order of activity against HCMV of the dihalobenzimidazole ribonucleosides was I ? Br ? CI >> F > H = CH3. The order of cytotoxicity among the most active compounds, however, was I > Br > Cl, thereby establishing that TCRB had the best antiviral properties.

Polysubstituted benzimidazoles as antiviral agents

This invention relates to novel polysubstituted benzimidazoles and compositions and their use in the treatment of viral infections. The polysubstituted benzimidazoles and compositions of the present invention exhibit antiviral properties against viruses of the herpes family, particularly human cytomegalovirus (HCMV) and herpes simplex viruses (HSV). Preferred polysubstituted benzimidazoles of the invention are 2,5,6-Trichloro-1-(β-D-5-deoxyribofuranosyl)benzimidazole and 2-bromo-5,6-dichloro-1-(5-deoxy-β-D-ribofuranosyl)benzimidazole.