90567-39-8

Basic information

• Product Name: 3-(HYDROXYMETHYL)-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-2(3H)-THIONE
• Synonyms: 3-(HYDROXYMETHYL)-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-2(3H)-THIONE;3-(hydroxymethyl)-5-(methylsulfanyl)-2,3-dihydro-1,3,4-thiadiazole-2-thione
• CAS NO: 90567-39-8
• Molecular Formula: C4H6N2OS3
• Molecular Weight: 194.3
• Mol File: 90567-39-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 72℃
• Boiling Point: 306.9°Cat760mmHg
• Flash Point: 139.4°C
• Appearance: /
• Density: 1.64g/cm³
• Vapor Pressure: 6.94E-05mmHg at 25°C
• Refractive Index: 1.771
• CAS DataBase Reference: 3-(HYDROXYMETHYL)-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-2(3H)-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(HYDROXYMETHYL)-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-2(3H)-THIONE(90567-39-8)
• EPA Substance Registry System: 3-(HYDROXYMETHYL)-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-2(3H)-THIONE(90567-39-8)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 90567-39-8(Hazardous Substances Data)

Usage

General Description

3-(hydroxymethyl)-5-(methylthio)-1,3,4-thiadiazole-2(3H)-thione is a chemical compound that belongs to the class of thiadiazole derivatives. It is known for its diverse biological activities, including antimicrobial, antifungal, and antiviral properties. 3-(HYDROXYMETHYL)-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-2(3H)-THIONE has been studied for its potential applications in the development of pharmaceuticals and agrochemicals. It has also been investigated for its antioxidant and anti-inflammatory properties. The chemical structure of 3-(hydroxymethyl)-5-(methylthio)-1,3,4-thiadiazole-2(3H)-thione makes it a promising candidate for further research and development in the fields of medicine and agriculture.

InChI:InChI=1/C4H6N2OS3/c1-9-3-5-6(2-7)4(8)10-3/h7H,2H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 6264-40-0 2-methylthio-5-mercapto-1,3,4-thiadiazole 

Relevant articles and documents

Chemistry of N-Heterocyclic Sulfur Compounds. Reaction of 2,5-Dimercapto-1,3,4-thiadiazoles with 1,ω-Dibromoalkanes. Synthesis of Tetrathia(2,5)-1,3,4-thiadiazolophanes and Dithia(3,5)-1,3,4-thiadiazolinophanedithiones

The base-catalyzed reaction of 2,5-dimercapto-1,3,4-thiadiazole (1) with 1,ω-dibromoalkanes Br(CH2)nBr (n=1-4) has been investigated.Model experiments on the alkylation of 2-mercapto-5-(methylthio)-1,3,4-thiadiazole (3) with 1,ω-dibromoalkanes and 2,5-bis-1,3,4-thiadiazoles, as well as on the dialkylation of 1 with 2--5-(methylthio)-1,3,4-thiadiazoles, have shown that both 3 and 1 undergo regioselective S-alkylation under basic conditions.However, the heterocyclization of 1 with 1,ω-dibromoalkanes and 2 equiv of KOH, carried out in EtOH under high dilution conditions, not only gave the expected S,S-bridgehead 2:2 macrocycles 2a (m=1; n=1,2,4), i.e., tetrathia(2,5)-1,3,4-thiadiazoles, but also the S,N-bridgehead 2:2 macrocycles 2b (m=1; n=2,3), i.e., dithia(3,5)-1,3,4-thiadiazolinophanedithiones.Furthermore, the high-dilution reaction of 1 with CH2Br2 and triethylamine gave 1,3,9,11,17,19-hexathia(2,5)-1,3,4-thiadiazolinophane (19) (2a: m=2; n=1), while the use of 1 equiv of KOH under moderate dilution resulted in the formation of the macrocyclic isomer 1,8,15-trithia(3,5)-1,3,4-thiadiazolinophane-4,11,18-trithione (20) (2b: m=2; n=1).The product distribution appears to be strongly dependent on the experimental conditions used, the nature and amount of base, the length of the dibromide, and its strength as an electrophilic agent.Several competing mechanisms have been ascertained to occur in the base-catalyzed heterocyclization of 1 with 1,ω-dibromoalkanes.The proposed reaction pathways gain support from the study of appropriate model reactions and from the isolation and identification of the involved key intermediates. 13C NMR spectroscopy has been extensively used to firmly establish the structures of the compounds obtained.