68468-39-3

Usage

Uses

Used in Research Processes:
5-Bromo-1,3-dihydro-2H-benzimidazol-2-thione is used as a research compound for its unique chemical structure, contributing to the advancement of scientific knowledge in the field of chemistry.
Used in Laboratory Synthesis:
5-Bromo-1,3-dihydro-2H-benzimidazol-2-thione is used as a reactant in laboratory synthesis, enabling the creation of new compounds and materials with potential applications in various industries.
Note: As there is limited information available regarding its potential biological activities or industrial applications, the uses listed above are based on the provided materials and may not be exhaustive. Further research and development may reveal additional applications for 5-BROMO-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-THIONE.

InChI:InChI=1/C7H5BrN2S/c8-4-1-2-5-6(3-4)10-7(11)9-5/h1-3H,(H2,9,10,11)

Upstream product

• 137-26-8 Thiram 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 75-15-0 carbon disulfide 
• 140-89-6 potassium ethyl xanthogenate 
• 875-51-4 4-Bromo-2-nitroaniline 
• 333-20-0 potassium thioacyanate 
• 128-04-1 sodium dimethyldithiocarbamate 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 1424375-33-6 C₂₄H₁₆BrN₅O₆S 
• 1424375-36-9 C₂₃H₁₃BrFN₅O₅S 
• 1424375-39-2 C₂₄H₁₃BrN₆O₅S 
• 1424375-08-5 C₁₆H₉BrN₄O₄S 
• 340739-76-6 2-((2,4-dinitrophenyl)sulphanyl)-5-bromobenzimidazole 
• 1254758-63-8 5-{[(5-bromo-1H-benzimidazol-2-yl)sulfanyl]acetyl}-2-chlorobenzenesulfonamide 
• 109892-65-1 2-(5-bromo-1(3)H-benzimidazol-2-ylmercapto)-propionic acid 
• 5450-30-6 (5-bromo-1(3)H-benzimidazol-2-ylmercapto)-acetic acid 
• 4887-88-1 5-bromo-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green chemistry metrics

A green and efficient method has been developed for the synthesis of 2-mercaptobenzazole derivatives via the reaction of commercially available aniline derivatives with low-cost and nontoxic potassium thiocyanate in water. The reactions proceeded smoothly under catalyst- and ligand-free conditions to give the corresponding products in good to excellent yields. The versatility, low cost, and environmental friendliness, in combination with high yields and easy work-up makes the procedure noteworthy.

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.

Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media

A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.

AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate

A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.

2-substituted thioacetamide compound, and preparation method and application thereof

The invention discloses a 2-substituted thioacetamide compound, and a preparation method and an application thereof. The structure of the 2-substituted thioacetamide compound is represented by formulaI, and R in the formula I is a C1-C3 alkoxy group, halogen or NR1R2, wherein R1 and R2 are H and a C1-C3 alkyl group independently. The compound can effectively inhibit protein-arginine methyltransferase 5, and can be used as a PRMT5 inhibitor.

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.

Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization

PRMT5 plays important roles in diverse cellular processes and is upregulated in several human malignancies. Besides, PRMT5 has been validated as an anticancer target in mantle cell lymphoma. In this study, we found a potent and selective PRMT5 inhibitor by performing structure-based virtual screening and hit optimization. The identified compound 17 (IC50 = 0.33 μM) exhibited a broad selectivity against a panel of other methyltransferases. The direct binding of 17 to PRMT5 was validated by surface plasmon resonance experiments, with a Kd of 0.987 μM. Kinetic experiments indicated that 17 was a SAM competitive inhibitor other than the substrate. In addition, 17 showed selective antiproliferative effects against MV4-11 cells, and further studies indicated that the mechanism of cellular antitumor activity was due to the inhibition of PRMT5 mediated SmD3 methylation. 17 may represent a promising lead compound to understand more about PRMT5 and potentially assist the development of treatments for leukemia indications.

Regioselective synthesis of isoxazole-mercaptobenzimidazole hybrids and their in vivo analgesic and anti-inflammatory activity studies

Regioselective synthesis of isoxazole-mercaptobenzimidazole hybrids and their efficiency in in vivo analgesic and anti-inflammatory activity was described. A comparison of structure-activity relationship for there compounds was also emphasized.

Inhibition of protein kinase C-driven nuclear factor-κB activation: Synthesis, structure-activity relationship, and pharmacological profiling of pathway specific benzimidazole probe molecules

A unique series of biologically active chemical probes that selectively inhibit NF-κB activation induced by protein kinase C (PKC) pathway activators have been identified through a cell-based phenotypic reporter gene assay. These 2-aminobenzimidazoles represent initial chemical tools to be used in gaining further understanding on the cellular mechanisms driven by B and T cell antigen receptors. Starting from the founding member of this chemical series 1a (notated in PubChem as CID-2858522), we report the chemical synthesis, SAR studies, and pharmacological profiling of this pathway-selective inhibitor of NF-κB activation.