27386-01-2

Basic information

• Product Name: 5-METHYLAMINO-[1,3,4]THIADIAZOLE-2-THIOL
• Synonyms: 1,3,4-Thiadiazole-2(3H)-thione, 5-(methylamino)-;5-Mercapto-2-methylamino-1,3,4-thiadiazole;5-methylamino-3H-1,3,4-thiadiazole-2-thione;InChI=1/C3H5N3S2/c1-4-2-5-6-3(7)8-2/h1H3,(H,4,5)(H,6,7;5-METHYLAMINO-[1,3,4]THIADIAZOLE-2-THIOL;TIMTEC-BB SBB010147;5-(methylamino)-1,3,4-thiadiazole-2(3H)-thione;1,3,4-Thiadiazole-2(3H)-thione,5-(methylamino)-(9CI)
• CAS NO: 27386-01-2
• Molecular Formula: C₃H₅N₃S₂
• Molecular Weight: 147.22
• EINECS: 248-436-2
• Product Categories: THIOL
• Mol File: 27386-01-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 190 °C
• Boiling Point: 207.6°Cat760mmHg
• Flash Point: 79.4°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 0.223mmHg at 25°C
• Refractive Index: 1.803
• CAS DataBase Reference: 5-METHYLAMINO-[1,3,4]THIADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLAMINO-[1,3,4]THIADIAZOLE-2-THIOL(27386-01-2)
• EPA Substance Registry System: 5-METHYLAMINO-[1,3,4]THIADIAZOLE-2-THIOL(27386-01-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 27386-01-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 4649, 1956 DOI: 10.1021/ja01599a033

InChI:InChI=1/C3H5N3S2/c1-4-2-5-6-3(7)8-2/h1H3,(H,4,5)(H,6,7)

Upstream product

• 6610-29-3 4-methylthiosemicarbazide 
• 38451-14-8 1,6-dimethyl-2,5-dithiobiurea 
• 75-15-0 carbon disulfide 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 65373-29-7 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-methylamine 
• 97773-03-0 2-(3-fluorobenzylthio)-5-methylamino-1,3,4-thiadiazole 
• 21111-48-8 5-methylamino-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 21123-49-9 N-methyl-N'-phenyl-[1,3,4]thiadiazole-2,5-diamine 
• 27386-03-4 4-benzyl-5-methylamino-2,4-dihydro-[1,2,4]triazole-3-thione 
• 27391-62-4 N-benzyl-N'-methyl-[1,3,4]thiadiazole-2,5-diamine 

Relevant articles and documents

Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents

Cancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.

Process for the production of 2-amino-5-mercapto-1,3,4-thiadiazole

2-Amino-5-mercapto-1,3,4-thiadiazoles can be produced in very high yields from thiosemicarbazides and carbon disulfide in aqueous phase by working in the presence of the corresponding ammonium salt of bis-2,5-mercapto-1,3,4-thiadiazole at a temperature above 40° C. Preferably the process is carried out in the presence of the mother liquor from a previous reaction.

Process for producing 2-amino or selected 2-(substituted)amino-5-mercapto-1,3,4-thiadiazole compounds

Disclosed is a process for producing 2-amino or 2-(lower alkyl or phenyl)amino-5-mercapto-1,3,4-thiadiazole compounds by reacting the corresponding thiosemicarbazide with an alkali metal lower alkyl xanthate salt.