68892-07-9

Basic information

• Product Name: METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE
• Synonyms: BUTTPARK 52\04-76;METHYL 1-METHYL-2-MERCAPTO-1H-5-IMIDAZOLECARBOXYLATE;METHYL 1-METHYL-2-MERCAPTO-1H-IMIDAZOLE-5-CARBOXYLATE;METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE;METHYL 2-MERCAPTO-1-METHYL-1H-IMIDAZOLE-5-CARBOXYLATE;methyl 2,3-dihydro-3-methyl-2-thioxo-1H-imidazole-4-carboxylate;2,3-Dihydro-3-methyl-2-thioxo-1H-imidazole-4-carboxylic acid methyl ester;methyl 3-methyl-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylate
• CAS NO: 68892-07-9
• Molecular Formula: C₆H₈N₂O₂S
• Molecular Weight: 172.2
• EINECS: 272-595-7
• Product Categories: blocks;Carboxes;Imidazoles
• Mol File: 68892-07-9.mol

Chemical Properties

• Melting Point: 188 °C
• Boiling Point: 240.6 °C at 760 mmHg
• Flash Point: 99.3 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 0.0376mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE(68892-07-9)
• EPA Substance Registry System: METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE(68892-07-9)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• HazardClass: IRRITANT
• Hazardous Substances Data: 68892-07-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE is used as a key intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique structure and reactivity contribute to the development of new and innovative medications.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE is utilized as a building block in the creation of effective and environmentally friendly pesticides and other agrochemical products.
Used in Organic Synthesis:
METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE is employed as a versatile reagent in organic synthesis, enabling the formation of a wide range of organic compounds for various applications.
Used in Medicinal Chemistry Research:
Due to its unique structure and functional groups, METHYL 1-METHYL-2-SULFANYL-1H-IMIDAZOLE-5-CARBOXYLATE is used as a valuable research tool in medicinal chemistry, aiding in the discovery and optimization of new therapeutic agents.

InChI:InChI=1/C6H8N2O2S/c1-8-4(5(9)10-2)3-7-6(8)11/h3H,1-2H3,(H,7,11)

Upstream product

• 107-31-3 Methyl formate 
• 68892-06-8 methyl N-formyl-N-methylglycinate 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 64038-57-9 (2-mercapto-3-methylimidazol-4-yl)methanoic acid 
• 17289-20-2 methyl 1-methyl-1H-imidazole-5-carboxylate 
• 1445985-54-5 (R)-methyl 2-((2,5-dichloro-4-((4-(4-cyclopropyl-1,2,3,4-tetrahydriquinoxaline-1-carbonyl)thiazolidin-3-yl)methyl)benzyl)thio)-1-methyl-1H-imidazole-5-carboxylate 
• 108905-63-1 Methyl 4-bromo-1-methyl-2-methylthio-5-imidazolecarboxylate 

Relevant articles and documents

New mixed-ligand ReV complexes with bis(2-mercaptoethyl) sulfide and functionalized thioimidazolyl ligands

The preparation of the mixed-ligand ReV complexes [Re(O)(κ3-SSS)(κ1-Simz)] (1), [Re(O)(κ3-SSS)(κ1-Simz)]·HCl (2) and [Re(O)(κ3-SSS)(κ1-SimzCOGlyGly)] (3) are described. These [3+1] type compounds are stabilized by tridentate bis(2-mercaptoethyl) sulfide (HSSSH) and by monodentate functionalized thioimidazolyl ligands. Complexes 1, 2 and 3 were fully characterized by IR and 1H NMR spectroscopy, and by X-ray diffraction analysis in the case of 1 and 2. In complexes 1 and 2 the Re atom is five-coordinate, presenting a distorted square pyramidal coordination geometry. Based on the angular structural parameter, τ, this distortion lies towards a trigonal bipyramidal geometry (τ = 0.40, 1; τ = 0.46, 2). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate

Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented.One proceeds from sarcosine via ring closure, bromination, and desulfurization.The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange.The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13).Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16).Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18).Subsequent dibromination gives the completely substituted imidazole 8.The primary purification in this sequence is fractional sublimation of 18 after the esterification step.An overall yield of 26percent is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.