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

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

Uses

Used in Chemical Synthesis:
(2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is used as a building block in chemical synthesis for its ability to participate in various chemical reactions due to the presence of the mercapto and hydroxyl groups.
Used in Pharmaceutical Research:
In pharmaceutical research, (2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is used as a molecular scaffold for the development of new drugs, leveraging the imidazole ring for potential interactions with biological targets and the mercapto and hydroxyl groups for further chemical modifications.
Used in Biochemical Applications:
(2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is used as a reagent in biochemical applications, taking advantage of its mercapto group for binding to other molecules, such as proteins or enzymes, for various biotechnological purposes.
Used in Material Science:
In material science, (2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is used as a component in the development of new materials, such as polymers or coatings, due to its ability to form stable covalent bonds and its potential to influence material properties.
Used in Analytical Chemistry:
(2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol is used as an analytical reagent in various detection and quantification methods, capitalizing on its chemical properties to selectively react with target analytes or enhance detection sensitivity.
Note: The specific applications listed above are inferred based on the compound's structural features and potential reactivity. The actual uses may vary and would require further research and development to confirm their practicality and effectiveness in each respective field.

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

Downstream Products

• 85012-71-1 5-hydroxymethyl-1-methyl-4-nitro-1H-imidazole 
• 85012-73-3 1-methyl-4-nitroimidazole-5-carbaldehyde 
• 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 
• 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 

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.

4,5-Disubstituted N-Methylimidazoles as Versatile Building Blocks for Defined Side-Chain Introduction

Fungerin is a 1,4,5-trisubstituted imidazole natural product characterised by a broad spectrum of antifungal activities. We planned to develop flexible strategies to access to such compounds. Imidazoles bearing suitable anchor groups at C-4 and C-5 allow the introduction of various substituted side-chains, generating libraries of fungerin derivatives for biological tests. Starting from commercially available reactants, two N-methyl 4,5-substituted imidazole core units were synthesised. Derivatives of type 1 contained two orthogonally protected C-1 anchors. Selective side-chain introduction was achieved through a sequence of Grignard coupling at C-5 to replace a tosylate and a Horner olefination through an aldehyde attached to C-4. Two target fungerin derivatives were synthesised. Since the organometallic substitution of the C-5-CH2-positioned leaving group proved to suffer from limitations concerning potential competing side-reactions, a type 2 imidazole core was built up. These structures had a halogen centre at C-4 and a hydroxyethyl anchor at C-5. Now, selective side-chain introduction allowed us to use Julia olefination to form the allyl side-chain at C-5 and Heck reactions to introduce the C-4 acryl substituents. Eight derivatives, including fungerin, were synthesised by this latter strategy, without producing any regioisomers. The second approach had the advantage that various side-chains could be coupled at C-4 and C-5 in two final steps. Thus, this strategy represents a versatile way to build up libraries of fungerin derivatives for biological testing.

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.

Preparation and structure determination of 1-benzyl-, 1-methyl- and 1H-5-[(2-nitro-2-phenyl)ethenyl]imidazoles

1-R-5-[(2-Nitro-2-phenyl)ethenyl]imidazoles (R = Bn, Me, H) 6a,b,c were synthesized by the Knoevenagel reaction of the corresponding aldehydes 4a,b,c with phenylnitromethane 5. The E-isomers 6a,b,c were precipitated from the reaction mixture as crystalline compounds in 89, 81 and 60% yields, respectively. Traces of the Z-isomers 6a'b',c' were found in the reaction mixtures but could be obtained in a ratio of 4:3 from the E-form with UV irradiation. The E-forms were more stable and the Z-isomers changed again to the E-isomers in several weeks.

An Effective Chirospecific Synthesis of (+)-Pilocarpine from L-Aspartic Acid

A short and efficient synthesis of (+)-pilocarpine (1) has been accomplished in 10 steps and 51percent overall yield from L-aspartic acid.The synthesis features a diastereoselective alkylation of a protected aspartic acid diester derivative and a selective hydrolysis of the α-methyl ester to give the corresponding amino acid.Subsequent replacement of the amino group with bromo, esterification, and a modified Reformatsky reaction with 1-methylimidazole-5-carboxaldehyde (8) afforded imidazole-substituted lactone 28.Details concerning this novel lactone synthesis are also described.Finally, hydrogenolysis of the lactone carbon-oxygen bond and selective reduction of the resulting monoester afforded pure (+)-pilocarpine (1).