27231-33-0

Basic information

• Product Name: 2H-Benzimidazole-2-thione,1,3-dihydro-4-methyl-(9CI)
• Synonyms: 2H-Benzimidazole-2-thione,1,3-dihydro-4-methyl-(9CI);2-MERCAPTO-4-METHYLBENZIMIDAZOLE;1,3-Dihydro-4-methyl-2H-benzimidazole-2-thione;4-methyl-1,3-dihydrobenzimidazole-2-thione;4-Methyl-1,3-dihydro-benzoimidazole-2-thione
• CAS NO: 27231-33-0
• Molecular Formula: C₈H₈N₂S
• Molecular Weight: 164.23
• Product Categories: BENZIMIDAZOLE
• Mol File: 27231-33-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 276.8±33.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 10.60±0.30(Predicted)
• CAS DataBase Reference: 2H-Benzimidazole-2-thione,1,3-dihydro-4-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Benzimidazole-2-thione,1,3-dihydro-4-methyl-(9CI)(27231-33-0)
• EPA Substance Registry System: 2H-Benzimidazole-2-thione,1,3-dihydro-4-methyl-(9CI)(27231-33-0)

Safety Data

• Hazardous Substances Data: 27231-33-0(Hazardous Substances Data)

Usage

General Description

2H-Benzimidazole-2-thione, 1,3-dihydro-4-methyl-(9CI) is a chemical compound with the molecular formula C9H9N3S. It is also known by other names such as 1,3-Dihydro-4-methyl-2H-benzimidazole-2-thione and 1,3-Dihydro-4-methylbenzimidazole-2-thione. This chemical is a derivative of benzimidazole and is commonly used in pharmaceutical research and drug development. It possesses potential medicinal properties and has been studied for its potential use in the treatment of various medical conditions. Its molecular structure and properties make it suitable for further investigation and potential application in the field of medicine and pharmacology.

Upstream product

• 75-15-0 carbon disulfide 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 128-04-1 sodium dimethyldithiocarbamate 
• 140-89-6 potassium ethyl xanthogenate 
• 82344-53-4 N,N-diacetyl-6-nitro-o-toluidine 
• 84445-92-1 2-amino-6-methylacetanilide 
• 59907-22-1 N-(2-methyl-6-nitrophenyl)acetamide 
• 570-24-1 2-Methyl-6-nitroaniline 
• 84445-89-6 1-acetyl-7-methyl-2-benzimidazolethiol 
• 137-26-8 Thiram 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 106747-42-6 2-[[(4-methyl-1H-benzimidazol-2-yl)thio]methyl]benzenamine 
• 170116-49-1 7-methyl-2-methylmercaptobenzimidazole 
• 4887-83-6 7-methyl-1H-benzo[d]imidazole 
• 106747-06-2 2-[[(4-methyl-1H-benzimidazol-2-yl)sulfinyl]methyl]benzenamine 

Relevant articles and documents

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.

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.

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.