223768-14-7

Basic information

• Product Name: 2-MERCAPTO-1-METHYLIMIDAZOLE
• Synonyms: TAPAZOLE;1,3-DIHYDRO-1-METHYL-2H-IMIDAZOL-2-THIONE;1-METHYL-2-IMIDAZOLETHIOL;1-METHYL-2-MERCAPTOIMIDAZOLE;1-METHYL-1H-IMIDAZOLE-2-THIOL;2-METHOXYCARBONYLAMINO-5-ISOPROPYLTHIO-1 H-BENZIMIDAZOLE;AKOS BBS-00004622;METHIAZOLE
• CAS NO: 223768-14-7
• Molecular Formula: C4H6N2S
• Molecular Weight: 114.17
• EINECS: 200-482-4
• Mol File: 223768-14-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 144-147 °C(lit.)
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-MERCAPTO-1-METHYLIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MERCAPTO-1-METHYLIMIDAZOLE(223768-14-7)
• EPA Substance Registry System: 2-MERCAPTO-1-METHYLIMIDAZOLE(223768-14-7)

Safety Data

• Hazard Codes: Xn
• Statements: 43-62-63
• Safety Statements: 26-27-36-45
• WGK Germany: 3
• RTECS: NI8615000
• Hazardous Substances Data: 223768-14-7(Hazardous Substances Data)

Usage

General Description

2-MERCAPTO-1-METHYLIMIDAZOLE, also known as MMI, is a chemical compound with the molecular formula C4H6N2S. It is a synthetic substance commonly used as a corrosion inhibitor in the production of water treatment chemicals and oil drilling fluids. MMI is also utilized in the pharmaceutical industry as a precursor in the production of antithyroid drugs, and as a stabilizer in the manufacture of photographic emulsions. It is a potent inhibitor of the enzyme thyroid peroxidase, which is responsible for the synthesis of thyroid hormones, and has potential applications in the treatment of hyperthyroidism. Additionally, MMI has shown potential as an anti-cancer agent and in the treatment of parasitic diseases, making it a versatile and valuable chemical compound in various industries.

Upstream product

• 64038-57-9 (2-mercapto-3-methylimidazol-4-yl)methanoic acid 
• 645-36-3 2,2-diethoxy-ethanamine 
• 556-61-6 methyl thioisocyanate 
• 333-20-0 potassium thioacyanate 
• 20677-73-0 N-methylaminoacetaldehyde diethyl acetal 
• 13733-17-0 isothiocyanoacetaldehyde diethyl acetal 
• 74-89-5 methylamine 
• 616-47-7 1-methyl-1H-imidazole 
• 61747-29-3 bis(1-methyl-1H-imidazole-2-yl)disulfide 
• 73395-65-0 anhydro-2-Hydroxy-8-methyl-4-oxo-3-phenyl-4H-imidazo<2,1-b><1,3>thiazinium hydroxide 
• 100-46-9 benzylamine 
• 90203-43-3 N-(2,2-diethoxy-ethyl)-N'-methyl-thiourea 
• 39799-77-4 1-methyl-1,3-dihydro-2H-imidazol-2-one 

Downstream Products

• 105402-18-4 1-hippuroyl-3-methyl-1,3-dihydro-imidazole-2-thione 
• 15033-66-6 1-benzoyl-3-methyl-1,3-dihydro-imidazole-2-thione 
• 15033-68-8 thiobenzoic acid S-(1-methyl-1H-imidazol-2-ylester); hydrochloride 
• 100142-91-4 3-methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid benzyl ester 
• 98134-95-3 carbimazole 
• 71370-42-8 1-Methylimidazol-2-yl)thioglycolsaeure 
• 98489-82-8 α-(1-methyl-1H-imidazol-2-ylmercapto)-isobutyric acid 
• 89517-92-0 1-methyl-1H-imidazole-2-sulfonic acid amide 
• 71370-34-8 7-methyl-3-oxo-2-phenyl-2,3-dihydro-imidazo[2,1-b]thiazolium betaine 
• 76808-29-2 2-(2-Oxo-1-phenyl-vinylsulfanyl)-imidazolidine-2-carbonitrile 
• 72208-78-7 2-phenyl-5,6-dihydro-imidazo[2,1-b]thiazol-3-one 
• 76794-60-0 C₁₂H₉N₃O₃S 
• 76794-59-7 6-Methyl-3-(4-nitro-phenyl)-1-oxa-4-thia-6,9-diaza-spiro[4.4]nona-2,7-diene-2-carbonitrile 

Relevant articles and documents

Preliminary evaluation of mesoionic 6-substituted 1-methylimidazo[2,1-b][1,3]thiazine-5,7-diones as potential novel prodrugs of methimazole

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Methimazole synthesizing and purifying method

The invention discloses a methimazole synthesizing and purifying method, and belongs to the field of medicine synthesis. The method comprises the following steps: carrying out a condensation reaction on methylaminoacetaldehyde polyethylene glycol and ammonium thiocyanate which are used as raw materials in the presence of an acid catalyst and a phase transfer catalyst; and adding saturated salt water after the reaction is completed, uniformly mixing the obtained reaction product and the saturated salt water, adding an organic solvent to carry out extraction, drying and concentrating the obtained organic layer to obtain crude methimazole, heating and dissolving the crude product in a solvent, adding active carbon to decolorize the obtained solution, filtering the solution, and drying the filtered solution to obtain purified methimazole. The method is a preparation method simple to operate and suitable for industrial production.

Synthesis and crystal structures of new 1,3-disubstituted imidazoline-2-thiones

Two methods (MeOH=K2CO3, pyridine=Et3N) were assessed for the introduction of sulfur into the 2-position of 1,3-disubstituted quaternary imidazolium salts 1-9 (Cl, I, BF4, PF6, CH3OSO3 were used as anions) to yield nine 1,3-disubstituted imidazoline-2-thiones 10-18 (1, 10: R1 = CH 3, R2 = CH3; 2, 11: R1 = OCH 2Ph, R2 = CH3; 3, 12: R1 = OCH 3, R2 = CH3; 4, 13: R1 = OCH 3, R2 = OCH3; 5, 14: R1 = NH 2, R2 = CH2Ph; 6, 15: R1 = NCHPh, R2 = CH3; 7, 16: R1 = NH2, R 2 = CH3; 8, 17: R1 = NCHPh, R2 = NCHPh; 9, 18: R1 = NH2, R2 = OCH3). Compounds 11-18 represent N-alkyloxy and N-amino imidazoline-2-thiones, whereas 10 served as reference compound. The first method was advantageous for the conversion 1 → 10 due to faster reaction, whereas in the reaction 2 → 11 considerable amounts of by-products were formed. Pure thiones 11, 14, 16, 17, and 18 were obtained only by the second method. Both methods worked for the synthesis of the methoxy derivatives 12 and 13 from 3 and 4, and the benzylideneamino derivative 15 from 6. 1-Amino-3- methylimidazoline-2-thione (16) was also prepared by hydrolysis of the benzylideneamino derivative 15. Crystal structures of seven 1,3-disubstituted imidazoline-2-thiones were determined by singlecrystal X-ray diffraction. Intermolecular C-H...S contacts were identified and, additionally, N-H...S interactions in aminothiones 14 and 16. The 1H NMR shifts of 10 and 13 were satisfactorily correlated with the Kamlet-Abboud-Taft π* and β parameters in ten solvents. From the lack of correlation with the a parameter and from the C=S bond length (average 1.68 A ) a significant contribution of a mesoionic imidazolium-2-thiolate resonance structure seems unlikely.