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

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

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

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 
• 116465-38-4 5,6-dichloro-1-phenyl-1H-benzo[d]imidazole 
• 142356-40-9 2-bromo-5,6-dichloro-1H-1,3-benzodiazole 

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.

Highly Diastereoselective Synthesis of Dihydro-benzoimidazo-[1,3]-thiazines via Electro-oxidative Selenocyclization of Thioallyl Benzoimidazoles

The current methodology reveals a green and proficient electro-oxidative tandem selenocyclization of thioallyl benzoimidazoles manufacturing selenylated dihydro-benzoimidazo-thiazine derivatives. Both C?Se and C?N bond formation were achieved via this mild protocol which exhibits good functional group tolerability affording an extensive range of substrate scope up to 96% isolated yields. Complete control over the regioselective formation of the six-membered heterocycle and stereoselective construction of the contiguous stereocenters was established. The practical electrochemical method operates in an undivided cell at ambient temperature without using any metal and external chemical oxidant.

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.

Novel and improved method for the synthesis of 2-mercaptobenzimidazole derivatives

2-mercaptobenzimidazole derivatives were synthesized by reaction of o-phenylenediamines with N-aminorhodanine. This reaction represent a new synthesis of 2-mercaptobenzazole. The structure of the obtained products was established by spectroscopic data.

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.

Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents

We herein report the synthesis, biological activity and structure-activity relationship of derivatives of 5,6-dichloro-1-β-d- ribofuranosylbenzimidazole and benzo[d]imidazole. A lead compound 6o demonstrates potent anti-proliferative activity and the ability to induce cancer cell apoptosis.

NOVEL VIRAL REPLICATION INHIBITOR

The present invention relates to a pharmaceutical composition for the treatment or prevention of viral infections comprising as an active principle at least one benzimidazole conjugates derivative havin the general formula I. The invention also relates to processes for the preparation of compounds according to the invention having above mentioned general formula and their use as a medicine or to treat or prevent viral infections.

Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.

Compounds 1-18 have been synthesized and tested in vitro against the protozoa Giardia lamblia, Entamoeba histolytica and the helminth Trichinella spiralis. Inhibition of rat brain tubulin polymerization was also measured and compared for each compound. Results indicate that most of the compounds tested were more active as antiprotozoal agents than Metronidazole and Albendazole. None of the compounds was as active as Albendazole against T. spiralis. Although only compounds 3, 9 and 15 (2-methoxycarbonylamino derivatives) inhibited tubulin polymerization, these were not the most potent antiparasitic compounds.

BENZIMIDAZOLE COMPOUNDS

A benzimidazole compound or a salt thereof which has an inhibitory action of forming of macrophages and is useful as an active ingredient of an orally available medicament for preventive and/or therapeutic treatment of arteriosclerosis, which is represented by the formula (I): wherein, R1 represents one or more functional groups on the benzene ring selected from the group consisting of hydrogen atom, a halogen atom, a lower alkyl group and a lower alkoxy group; R2 represents hydrogen atom, an alkyl group or an acyl group; L represents a C4-C8 alkylene group or an ethyleneoxy linking group represented as (CH2CH2O)nCH2CH2 wherein n represents 1 or 2; X represents O or NH; Y represents S or a single bond; and Q represents a 5- or 6-membered heterocyclic group which may have a functional group on the ring.