19462-98-7

Basic information

• Product Name: 5,6-DICHLOROBENZIMIDAZOLE-2-THIOL
• Synonyms: 5,6-DICHLOROBENZIMIDAZOLE-2-THIOL;5,6-DICHLORO-2-MERCAPTOBENZIMIDAZOLE;5,6-DICHLORO-1H-BENZO[D]IMIDAZOLE-2-THIOL;5,6-DICHLORO-1H-BENZIMIDAZOLE-2-THIOL;5,6-Dichloro-1H-benzo[d]imidazole-2-thiol, 95+%;5,6-Dichloro-1H-benzo[d]imidazole-2-thiol, 5,6-Dichloro-2-mercaptobenzimidazole;5,6-dichloro-1H-1,3-benzodiazole-2-thiol;5,6-dichloro-1,3-dihydrobenzimidazole-2-thione
• CAS NO: 19462-98-7
• Molecular Formula: C₇H₄Cl₂N₂S
• Molecular Weight: 219.09
• Mol File: 19462-98-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 329.8°Cat760mmHg
• Flash Point: 153.3°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 0.000173mmHg at 25°C
• Refractive Index: 1.755
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.76±0.30(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 5,6-DICHLOROBENZIMIDAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DICHLOROBENZIMIDAZOLE-2-THIOL(19462-98-7)
• EPA Substance Registry System: 5,6-DICHLOROBENZIMIDAZOLE-2-THIOL(19462-98-7)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: 36/37/38
• Safety Statements: 26-37
• Hazardous Substances Data: 19462-98-7(Hazardous Substances Data)

Usage

Description

5,6-DICHLOROBENZIMIDAZOLE-2-THIOL is an organic compound with the molecular formula C7H4Cl2N2S. It is a derivative of benzimidazole, a heterocyclic compound consisting of a benzene ring fused to an imidazole ring. The presence of two chlorine atoms at the 5,6-positions and a thiol group at the 2-position gives this compound unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5,6-DICHLOROBENZIMIDAZOLE-2-THIOL is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the synthesis of new drugs with potential therapeutic applications.
Used in Antiviral Applications:
In the pharmaceutical industry, 5,6-DICHLOROBENZIMIDAZOLE-2-THIOL is employed as a key component in the synthesis of 2',3'-dideoxy and 2',3'-unsaturated ribofuranonucleosides. These nucleoside analogs have shown potential as antiviral agents, making this compound an important contributor to the development of new antiviral therapies.
Used in Chemical Research:
5,6-DICHLOROBENZIMIDAZOLE-2-THIOL can also be used as a research tool in various chemical studies. Its unique structure and functional groups make it an interesting candidate for exploring new reaction pathways, understanding molecular interactions, and developing novel synthetic strategies.

InChI:InChI=1/C7H4Cl2N2S/c8-3-1-5-6(2-4(3)9)11-7(12)10-5/h1-2H,(H2,10,11,12)

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 
• 1438-16-0 3-aminorhodanine 
• 6306-39-4 1,2-dichloro-4,5-dinitrobenzene 
• 95-50-1 1,2-dichloro-benzene 
• 137-26-8 Thiram 

Downstream Products

• 156385-61-4 S²-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-mercapto-5,6-dichlorobenzimidazole 
• 156385-59-0 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-mercapto-5,6-dichlorobenzimidazole 
• 156385-60-3 1,3-bis(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thio-5,6-dichlorobenzimidazole 
• 20076-54-4 5,6-dichloro-2-(methylthio)-1H-benzo[d]imidazole 
• 16865-11-5 2,5,6-trichloro-1H-benzo[d]imidazole 
• 53-85-0 5,6-dichloro-1-β-D-ribobenzimidazole 

Relevant articles and documents

Benzimidazole Ribonucleosides: Design, Synthesis, and Antiviral Activity of Certain 2-(Alkylthio)- and 2-(Benzylthio)-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazoles

Several 2-alkylthio and 2-benzylthio derivatives of 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (DRB) have been designed and synthesized from 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole-2-thione.All compounds were evaluated for activity against hu

Design, synthesis, and antitumor activity of PLGA nanoparticles incorporating a discovered benzimidazole derivative as EZH2 inhibitor

Purpose: Targeting enhancer of zeste homolog 2 (EZH2) can represent a hopeful strategy for oncotherapy. Also, the use of PLGA-based nanoparticles as a novel and rate-controlling carrier system was of our concern. Methods: Benzimidazole derivatives were synthesized, and their structures were clarified. In vitro antitumor activity was evaluated. Then, a modeling study was performed to investigate the ability of the most active compounds to recognize EZH2 active sites. Compound 30 (Drug) was selected to conduct pre-formulation studies and then it was incorporated into polymeric PLGA nanoparticles (NPs). NPs were then fully characterized to select an optimized formula (NP4) that subjected to further evaluation regarding antitumor activity and protein expression levels of EZH2 and EpCAM. Results: The results showed the antitumor activity of some synthesized derivatives. Docking outcomes demonstrated that Compound 30 was able to identify EZH2 active sites. NP4 exhibited promising findings and proved to keep the antitumor activity of Compound 30. HEPG-2 was the most sensitive for both Drug and NP4. Protein analysis indicated that Drug and NP4 had targeted EZH2 and the downstream signaling pathway leading to the decline of EpCAM expression. Conclusions: Targeting EZH2 by Compound 30 has potential use in the treatment of cancer especially hepatocellular carcinoma.

An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water

An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.

Synthesis and antiprotozoal activity of novel 2-{[2-(1H-imidazol-1-yl) ethyl]sulfanyl}-1H-benzimidazole derivatives

A series of 19 new 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives was synthesized starting from the properly substituted 1,2-phenylendiamine. These compounds have hydrogen or methyl at position 1; while hydrogen, chlorine, ethoxy or methoxycarbonyl group is at position 5 and/or 6. The novel compounds were tested against protozoa Trichomonas vaginalis, Giardia intestinalis and Entamoeba histolytica. Experimental evaluations revealed strong activity for all tested compounds, having IC 50 values in the nanomolar range, which were even better than metronidazole, the drug of choice for these parasites.