17452-74-3

Basic information

• Product Name: 5-methyl-1,3,4-oxathiazol-2-one
• Synonyms: 5-methyl-1,3,4-oxathiazol-2-one;5-Methyl-1,3,4-oxathiazole-2-one
• CAS NO: 17452-74-3
• Molecular Formula: C₃H₃NO₂S
• Molecular Weight: 117.12642
• Mol File: 17452-74-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 145.4°C at 760 mmHg
• Flash Point: 41.7°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 4.87mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 5-methyl-1,3,4-oxathiazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-1,3,4-oxathiazol-2-one(17452-74-3)
• EPA Substance Registry System: 5-methyl-1,3,4-oxathiazol-2-one(17452-74-3)

Safety Data

• Hazardous Substances Data: 17452-74-3(Hazardous Substances Data)

Usage

General Description

5-methyl-1,3,4-oxathiazol-2-one is a chemical compound with the molecular formula C5H5NOS. It is an oxathiazinone derivative and belongs to the class of organic compounds known as heteroaromatic compounds. 5-methyl-1,3,4-oxathiazol-2-one has a five-membered ring with oxygen, sulfur, and nitrogen atoms. It is used in the synthesis of pharmaceutical products, agrochemicals, and other organic compounds. It has also been studied for its potential biological activities and pharmacological properties. Additionally, 5-methyl-1,3,4-oxathiazol-2-one has been used as a building block in organic synthesis for the preparation of various functionalized molecules.

InChI:InChI=1/C3H3NO2S/c1-2-4-7-3(5)6-2/h1H3

Upstream product

• 60-35-5 acetamide 
• 2757-23-5 chloro(chlorosulfanyl)methanone 

Downstream Products

• 50483-77-7 3-Methyl-5-phenyl-1,2,4-thiadiazole 
• 49570-33-4 4,5-Bis(carbomethoxy)-3-methyl-1,2-thiazole 
• 119-61-9 benzophenone 
• 117053-94-8 3-Methyl-5,5-diphenyl-[1,4,2]dithiazole 
• 75-05-8 acetonitrile 
• 76162-56-6 ethyl 3-methyl-1,2,4-thiadiazole-5-carboxylate 
• 126472-35-3 3-Phenyl-[1,2]thiaphosphole-4,5-dicarboxylic acid dimethyl ester 
• 120587-95-3 3,5-Diphenyl-[1,2,4]thiadiphosphole 

Relevant articles and documents

Synthesis and biological evaluation of novel isothiazoloquinoline quinone analogues

Natural quinones and their analogues have attracted growing attention because of their novel anticancer activities. A series of novel isothiazoloquinoline quinone analogues were synthesized and evaluated for antitumor activities against four different kind of cancer cells. Among them, isothiazoloquinolinoquinones inhibited cancer cells proliferation effectively with IC50 values in the nanomolar range, and isothiazoloquinolinoquinone 13a induced the cell apoptosis. Further exploration of possible mechanism of action indicates that 13a not only activates ROS production through NQO1-directed redox cycling but also inhibits the phosphorylation of STAT3. These findings indicate that 13a has potential use for the development of new skeleton drug candidate as an efficient substrate of NQO1 and STAT3 inhibitor.

Structure and stability of small nitrile sulfides and their attempted generation from 1,2,5-thiadiazoles

The gas-phase generation and spectroscopic identification of nitrile sulfides by thermolysis of 1,2,5-thiadiazole precursors was attempted, but in all cases the thiadiazoles were found to produce sulfur and the corresponding nitrile. This prompted an investigation by ab initio and density functional calculations for the equilibrium geometries, stabilities, and decomposition mechanisms of several nitrile sulfides (XCNS, where X = H, F, Cl, CN, CH3). Equilibrium geometries obtained from calculations at the B3LYP, MPn(n = 2-4), QCISD, QCISD(T), CCSD, and CCSD(T) levels with moderate to large basis sets indicate that the molecules have linear heavy atom geometries. The exception is the fluoro derivative, which is bent with a calculated barrier to linearity of 889 cm-1 (B3LYP/cc-pVTZ). The nitrile sulfides are predicted by the B3LYP method to be stable in the dilute gas phase, whereas in the condensed phase they are suggested to be very unstable due to bimolecular decomposition. The mechanism of this loss process is complicated by various sulfur transfer and cyclization reactions between decomposition intermediates, with the predicted stable products being sulfur, nitriles, and thiadiazoles. The first step of the bimolecular decomposition is either a cycloaddition to thiofuroxan or a sulfur transfer with simultaneous S2 loss to nitriles.