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

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

Uses

Used in Organic Synthesis:
5,6-Dibromo-2-chloro-1H-1,3-benzodiazole is used as a building block in organic synthesis for the creation of various complex organic molecules. Its presence of bromine and chlorine atoms allows for versatile chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole is utilized as a key intermediate in the development of new drugs. Its unique structure and reactivity contribute to the design and synthesis of potential therapeutic agents, particularly those targeting specific biological pathways or diseases.
Used in Agrochemical Development:
5,6-Dibromo-2-chloro-1H-1,3-benzodiazole may also have potential applications in the development of new agrochemicals. Its chemical properties can be harnessed to create compounds that address various agricultural needs, such as pest control or crop protection.
Used in Research and Development:
Due to its distinctive chemical characteristics, 5,6-Dibromo-2-chloro-1H-1,3-benzodiazole is a valuable resource for researchers studying benzodiazole chemistry. It aids in the exploration of the compound's biological activities and potential applications in various fields, including medicine and agriculture.

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)

Synthesis and Cyclization of Derivatives of 3-Heterylhydrazino-2-polyfluorobenzoylacrylic Acid

Cyclization of ethyl esters of 3-heterylhydrazino-2-polyfluorobenzoylacrylic acid results either to 2-(5-polyfluorophenyl-4-ethoxycarbonylpyrazol-1-yl)benzazoles or 2-(4-polyfluorobenzoyl-5-ethoxypyrazol-1-yl)benzenes or, in the case of benzimidazolyl derivatives possessing NH fragment, to derivatives of benzimidazolo[1,2-a]pyrazolo[1,5-c]quinazoline, a new heterocyclic system.

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

Polysubstituted benzimidazoles and pharmaceutical compositions containing them as the active ingredients. These compounds and compositions exhibit antiviral activity against viruse of the herpes family, particularly human cytomegalovirus and herpes simplex viruses (HSV).

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.