27231-37-4

Basic information

• Product Name: (5-METHYL-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETIC ACID
• Synonyms: (5-METHYL-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETIC ACID;CHEMBRDG-BB 4140363;ASINEX-REAG BAS 16289554;TIMTEC-BB SBB011493;((5-METHYL-1H-BENZIMIDAZOL-2-YL)THIO)ACETIC ACID;[(5-methyl-1H-benzimidazol-2-yl)thio]acetic acid(SALTDATA: 0.5H2O)
• CAS NO: 27231-37-4
• Molecular Formula: C₁₀H₁₀N₂O₂S
• Molecular Weight: 222.26
• Mol File: 27231-37-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 480.7°C at 760 mmHg
• Flash Point: 244.5°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 4.75E-10mmHg at 25°C
• Refractive Index: 1.7
• CAS DataBase Reference: (5-METHYL-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5-METHYL-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETIC ACID(27231-37-4)
• EPA Substance Registry System: (5-METHYL-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETIC ACID(27231-37-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 27231-37-4(Hazardous Substances Data)

Usage

General Description

"(5-Methyl-1H-benzoimidazol-2-ylsulfanyl)-acetic acid" is a chemical compound with the molecular formula C11H11N3O2S. It is an organic compound with a benzimidazole ring structure, containing a sulfur atom attached to a methyl group and an acetic acid moiety. (5-METHYL-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETIC ACID is commonly used in the pharmaceutical industry for the synthesis of various drugs due to its potential medicinal properties. It is also known for its role as a chelating agent and as an intermediate in organic synthesis. Additionally, it has been studied for its potential anti-inflammatory and antioxidant properties, making it a promising compound in the development of therapeutic agents.

InChI:InChI=1/C10H10N2O2S/c1-6-2-3-7-8(4-6)12-10(11-7)15-5-9(13)14/h2-4H,5H2,1H3,(H,11,12)(H,13,14)

Upstream product

• 496-72-0 4-methyl-1,2-diaminobenzene 
• 79-11-8 chloroacetic acid 
• 27231-36-3 5-methyl-1H-benzoimidazole-2-thiol 
• 27231-36-3 5-methyl-2-benz-1,3-imidazoline-2-thione 

Downstream Products

• 27231-42-1 2-(4-dimethylamino-benzylidene)-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-50-1 2-bromo-2-[bromo-(4-dimethylamino-phenyl)-methyl]-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-49-8 2-bromo-2-[bromo-(4-methoxy-phenyl)-methyl]-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-48-7 2-bromo-2-[bromo-(4-chloro-phenyl)-methyl]-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-47-6 2-bromo-2-(bromo-phenyl-methyl)-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-43-2 2-(4-methoxy-benzylidene)-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-41-0 2-(4-chloro-benzylidene)-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 27231-40-9 2-benzylidene-6-methyl-benzo[4,5]imidazo[2,1-b]thiazol-3-one 

Relevant articles and documents

Tautomerism and isomerism in some antitrichinellosis active benzimidazoles: Morphological study in polarized light, quantum chemical computations

The morphology of the crystal structure of some antitrichinellosis active benzimidazole derivatives including (1H-benzimidazol-2-ylthio)acetic acids, [1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones, 1H-benzimidazol-2-ylthioacetylpiperazines and starting 2-mercapto benzimidazoles, was studied by the use of Polarized Light Microscopy (PLM). Characterization of the crystal phase was complimented by Differential scanning calorimetry analysis (DSC) and spectroscopic data. DFT computations were performed in order to investigate the prototropic tautomerism and the geometry of the molecule of the synthesized compounds. One distinct type of crystal structure for each one of 5 or 6-methyl-(1H-benzimidazol-2-ylthio)acetic acid 6 was observed by PLM – dendritic and needle-shaped formations. Compound 14, containing a methyl substituent in the benzimidazole ring crystallized also into two phases; while for the unsubstituted compound 13 a separation of phases does not take place. The influence of the both solvents - chloroform and ethanol on the phase separation and the formation of the crystalline structure of compound 14 was investigated. The morphological study showed that the cyclization of 6 in the presence of acetic anhydride in pyridine medium led to a mixture of 6-methyl-[1,3]tiazolo[3,2-a]benzimidazol-3(2H)-one (10a) and 7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one (10b), which crystallized in the form of fibrils and spherulites respectively. It was found that a difference in the crystal structures of substituted and unsubstituted benzimidazol-2-thiones, respectively benzimidazol-2-thiol derivatives exists, which may be due not only to the thiol-thione tautomerism but to the prototropic properties of the hydrogen atom in first position of the ring. The calculation results indicated that the thione form is more stable than the thiol tautomer by 51–55 kJ mol?1. But at the same time ΔG for the two thiol tautomers is below 0.5 kJ mol?1. In solid phase the 5(6)-substituted-1H-benzimidazol-2-thiols crystallized in two different crystal structures while the unsubstituted 1H-benzimidazol-2-thiol possess one type of crystal structure.

Synthesis and antitrichinellosis activity of some 2-substituted-[1,3] thiazolo[3,2-a]benzimidazol-3(2H)-ones

Some new thiazolo[3,2-a]benzimidazolone derivatives were synthesized using two methods. The structures of the synthesized compounds were proved by means of IR, 1H NMR and mass spectral data. Ab initio computations were performed in order to determine the electronic structure and geometry of the investigated molecules and to compare it to the geometry of albendazole. Biologically, experiments in vitro and in vivo were accomplished in order to identify the efficacy of the obtained thiazolobenzimidazolones against Trichinella spiralis. The effectiveness of compounds 4a-c in the intestinal phase of trichinellosis was 100% and in the muscle phase were 88% and 80% at a concentration of 100 mg/kg mw for the compounds 4a and 4c. The results of the hepatotoxicity test showed that the compounds 4a and 4b possess hepatotoxicity comparable to that of albendazole.

HETEROCYCLIC SYSTEMS CONTAINING BRIDGEHEAD NITROGEN ATOM-7

The synthesis of 6-methyl- , 8- methyl- , 6,7- dimethyl- , and 5,8- dimethyl-thiazolo !3,2- alpha! benzimidazol- c(2H)- ones and 2H- 7,8-dimethyl !1,3! thiazino !3,3- alpha! benzimidazol- 4(3H)- one have been accomplished by the cyclization with acetic anhydride of the corresponding acid. The orientation of the product formed, wherever two isomeric products are likely to be obtained on cyclization, has been established through NMR spectral data. The condensation of some thiazolidinoines with aldehydes and their bromine derivatives have also been studied.