143122-18-3

Basic information

• Product Name: (2-MERCAPTO-1-METHYL-1H-IMIDAZOL-5-YL)METHANOL
• Synonyms: 5-(HYDROXYMETHYL)-2-MERCAPTO-1-METHYLIMIDAZOLE;(3-METHYL-2-SULFANYL-1H-3LAMBDA5-IMIDAZOL-4-YL)METHANOL;(2-MERCAPTO-1-METHYL-1H-IMIDAZOL-5-YL)METHANOL;2-Mercapto-1-methylimidazole-5-methanol;(2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol, tech;4-(Hydroxymethyl)-2-mercapto-1-methylimidazole;4-(hydroxymethyl)-3-methyl-1H-imidazole-2-thione
• CAS NO: 143122-18-3
• Molecular Formula: C₅H₈N₂OS
• Molecular Weight: 144.19
• Mol File: 143122-18-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 223-226°C
• Boiling Point: 258.9 °C at 760 mmHg
• Flash Point: 110.4 °C
• Appearance: /
• Density: 1.39 g/cm³
• Vapor Pressure: 0.00196mmHg at 25°C
• Refractive Index: 1.68
• PKA: 11.92±0.70(Predicted)
• CAS DataBase Reference: (2-MERCAPTO-1-METHYL-1H-IMIDAZOL-5-YL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2-MERCAPTO-1-METHYL-1H-IMIDAZOL-5-YL)METHANOL(143122-18-3)
• EPA Substance Registry System: (2-MERCAPTO-1-METHYL-1H-IMIDAZOL-5-YL)METHANOL(143122-18-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 143122-18-3(Hazardous Substances Data)

Usage

General Description

(2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is a chemical compound that is composed of a methyl group attached to an imidazole ring, with a mercapto (sulfhydryl) group and a hydroxyl group attached to the imidazole ring. (2-MERCAPTO-1-METHYL-1H-IMIDAZOL-5-YL)METHANOL has potential applications in chemical synthesis and pharmaceutical research due to its unique structure and functional groups. The mercapto group can participate in various chemical reactions, while the imidazole ring provides a site for potential interactions with biological molecules. The presence of the methyl group and the hydroxyl group also adds further versatility to this compound’s potential uses in chemical and biological systems. Overall, (2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is a versatile chemical compound with potential applications in various fields.

InChI:InChI=1/C5H8N2OS/c1-7-4(3-8)2-6-5(7)9/h2,8H,3H2,1H3,(H,6,9)

Upstream product

• 96-26-4 dihydroxyacetone 
• 333-20-0 potassium thioacyanate 
• 74-89-5 methylamine 
• 62147-49-3 1,3-dihydroxyacetone dimer 
• 593-51-1 methylamine hydrochloride 

Downstream Products

• 141524-74-5 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde 
• 924869-11-4 2-((3,4-dichlorobenzyl)thio)-1-methyl-1H-imidazole-5-carbaldehyde 
• 338422-40-5 (2-((4-fluorobenzyl)thio)-1-methyl-1H-imidazol-5-yl)methanol 
• 1427210-51-2 10-(1-methyl-2-(methylthio)-1H-imidazol-5-yl)-5-phenyl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione 
• 1307804-06-3 2-(1-methyl-2-methylsulfonyl-1H-imidazol-5-yl)-5-(benzylsulfonyl)-1,3,4-thiadiazole 
• 1307804-02-9 2-(1-methyl-2-methylsulfonyl-1H-imidazol-5-yl)-5-(benzylthio)-1,3,4-thiadiazole 
• 182965-63-5 1-Methyl-5-((E)-2-nitro-2-phenyl-vinyl)-1H-imidazole 
• 191411-54-8 (Z)-2-Azido-3-(2-benzylsulfanyl-3-methyl-3H-imidazol-4-yl)-acrylic acid ethyl ester 
• 191411-64-0 2-Benzylsulfanyl-1-methyl-1,4-dihydro-pyrrolo[2,3-d]imidazole-5-carboxylic acid ethyl ester 
• 191411-50-4 2-Benzylsulfanyl-3-methyl-3H-imidazole-4-carbaldehyde 
• 384821-16-3 tris{5-[(4'-methoxyphenyl)methoxymethyl]-1-methyl-1H-2-imidazolyl}methyl methyl ether 
• 384821-15-2 tris{5-[(4'-methoxyphenyl)methoxymethyl]-1-methyl-1H-2-imidazolyl}methyl alcohol 
• 384821-29-8 bis(N-allyl-N-methyl-5'-aminomethyl-1'-methyl-1'H-2'-imidazolyl)[1''-(2''-methoxyphenyl)-1'H-2'-imidazolyl]methyl alcohol 
• 384821-30-1 bis(N-allyl-N-methyl-5'-aminomethyl-1'-methyl-1'H-2'-imidazolyl)[1''-(2''-methoxyphenyl)-1'H-2'-imidazolyl]methyl methyl ether 

Relevant articles and documents

Design, Synthesis, and Docking Studies of Thioimidazolyl Diketoacid Derivatives Targeting HIV-1 Integrase

Background: Integrase enzyme is a validated drug target to discover novel structures as anti-HIV-1 agents. Objective: This study aimed at developing a novel series of thioimidazolyl diketoacid derivatives characterizing various substituents at N-1 and 2-thio positions of the central ring as HIV-1integrase inhibitors. Methods: In this study, eighteen novel thioimidazolyl DKA derivatives were synthesized in a five-step parallel procedure and tested in vitro for the inhibition of both IN ST reaction and the single-cycle HIV-1 replication in HeLa cell culture. Results: The obtained molecules were evaluated using the enzyme assay, displaying promising integrase inhibitory activity with IC50 values ranging from 0.9 to 7.7 mM. The synthesized compounds were also tested for antiviral activity and cytotoxicity using HeLa cells infected by the single-cycle replicable HIV-1 NL4-3. Conclusion: The most potent compound was found to be 18i with EC50 = 19 μM, IC50 = 0.9 μM, and SI = 10.5. Docking studies indicated that the binding mode of the active molecule is well aligned with the known HIV-1integrase inhibitor.

Synthesis and antiproliferative activity evaluation of imidazole-based indeno[1,2-b]quinoline-9,11-dione derivatives

A series of new imidazole substituted indeno[1,2-b]quinoline-9,11-dione derivatives were synthesized and evaluated for their antiproliferative effects on HeLa, LS180, MCF-7 and Jurkat human cancer cell lines. Antiproliferative effects were evaluated using MTT assay. Prepared compounds exhibited weak to good antiproliferative activity in evaluated cell lines. Prepared compounds were more potent in Jurkat cell line when compared to LS180, HeLa and MCF-7 cell lines. Compounds 29 (IC16 = 0.7 μM) and 31 (IC16 = 1.7 μM) and 33 (IC16 = 1.7 μM) were found to be the most potent molecules on Jurkat cell lines. Moreover; it was found that some of the tested compounds bearing imidazole-2-yl moiety on the C11-position of dihydropyridine ring exhibited superior antiproliferative activity in comparison to cis-platin especially in Jurkat cell line (compounds 29, 31, and 33). It seemed that the introduction of electron-withdrawing groups on the imidazole ring enhanced the antiproliferative potential of these compounds (compounds 27, 29 and 31). The results of this study proposed that some of the imidazole substituted indeno[1,2-b]quinoline-9,11-dione compounds may act as efficient anticancer agents in vitro, emphasizing their potential role as a source for rational design of potent antiproliferative agents.

Synthesis and anti-inflammatory activity of new 1-methyl-4-(4-X-benzenesulfonyl)pyrrolo[2,3-d] imidazole-5-carboxylates

A series of 1-methyl-4-(4-X-arylsulfonyl)pyrrolo[2,3-d]imidazole-5-carboxylates were synthesized and tested as anti-inflammatory agents. Indomethacin was used as reference drug. Two of the synthesized compounds 7a and 7b had an effect equal to 0.1 of indomethacin. Our result showed that the electron-withdrawing substituents in the para position of the benzensulfonyl moiety increase activity.