4756-05-2

Basic information

• Product Name: thioacetone
• Synonyms: thioacetone;2-Propanethione;Dimethyl thioketone;Dimethylmethylenesulfur(IV);Propane-2-thione
• CAS NO: 4756-05-2
• Molecular Formula: C₃H₆S
• Molecular Weight: 0
• Mol File: 4756-05-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 68.1°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.89g/cm³
• Vapor Pressure: 212mmHg at 25°C
• Refractive Index: 1.471
• CAS DataBase Reference: thioacetone(CAS DataBase Reference)
• NIST Chemistry Reference: thioacetone(4756-05-2)
• EPA Substance Registry System: thioacetone(4756-05-2)

Safety Data

• Hazardous Substances Data: 4756-05-2(Hazardous Substances Data)

Usage

General Description

Thioacetone, also known as 2,2-dimethyl-1,3-dithiolane, is a highly foul-smelling organic compound with the chemical formula (CH3)2CS. It is a colorless liquid with a garlic-like odor that is so potent, it can cause nausea, vomiting, and even unconsciousness in low concentrations. Thioacetone is primarily used in organic synthesis and as a cross-linking agent in rubber production. Due to its extremely unpleasant smell and potential health hazards, thioacetone is handled with extreme caution and is not commonly encountered outside of industrial settings.

InChI:InChI=1/C3H6S/c1-3(2)4/h1-2H3

Upstream product

• 14252-45-0 2,2-bis(ethylthio)propane 
• 814-67-5 1,2-propanedithiol 
• 102505-69-1 1-<2-<(2-chloroethyl)sulfinyl>-2,2-dimethylethyl>-3-tert-butyl-1-nitrosourea 
• 67-64-1 acetone 
• 38739-06-9 S-isopropyl isopropanethiosulfinate 
• 705256-38-8 3,3,5,5-tetramethyl-1,2,4-trithiolane 1-oxide 
• 705256-39-9 3,3,5,5-tetramethyl-1,2,4-trithiolane-4-oxide 
• 594-20-7 2,2-dichloropropane 
• 40852-89-9 i-propylidene diradical 
• 83984-34-3 1-<2-<(2-chloroethyl)sulfinyl-18O>-2,2-dimethylethyl>-3-cyclohexyl-1-nitrosourea 
• 83984-33-2 1-<2-<(2-chloroethyl)sulfinyl-18O>-1,1,2,2-tetramethylethyl>-3-tert-butyl-1-nitrosourea 
• 102505-60-2 1-<2-<(2-chloroethyl)sulfinyl>-1,1,2,2-tetramethylethyl>-3-tert-butyl-1-nitrosourea 
• 135986-79-7 2-methyl-2-thiol propionitrile 
• 563-79-1 2,3-Dimethyl-2-butene 

Downstream Products

• 65739-85-7 3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzoxazine-6-thione 
• 142671-63-4 3,4,4-trimethyl-2-oxothietan-3-yl acetate 
• 174497-93-9 2'-O-methylthiomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 4933-34-0 2-propanethial S-oxide 
• 201287-93-6 4-(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 
• 359451-16-4 [6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]ethanone 
• 1379475-36-1 5-acetyl-6-methyl-4-(2,6-dichlorophenyl)-3,4-dihydropyrimidine-2(1H)-thione 
• 405154-01-0 5-acetyl-6-methyl-4-(2-fluorophenyl)-3,4-dihydropyrimidine-2(1H)-thione 
• 1290637-13-6 5-methyl-6-(2-thienylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 144459-98-3 5-methylcarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 828-26-2 hexamethyl-[1,3,5]trithiane 
• 135986-82-2 3,4,6,6-tetramethyl-1-thiacyclohex-3-ene 

Relevant articles and documents

Thermolysis of 3,3,5,5-tetramethyl-1,2,4-trithiolane 1-oxide: First matrix isolation of the HOSS· radical

Flash vacuum pyrolysis of 3,3,5,5-tetramethyl-1,2,4-trithiolane 1-oxide performed at 700 °C yields the 1-oxatrisulfan-3-yl radical (HOSS ·) along with disulfur monoxide (S2O) and diisopropyl sulfide, which were isolated in argon matrices at 10 K. Upon irradiation with UV light, the 1-oxatrisulfan-3-yl radical undergoes isomerization to the 1-oxatrisulfan-1-yl radical (HSSO·). Both radicals were identified by comparison of their computed and experimental IR and UV/Vis spectra. In addition, density functional theory (DFT) computations offer a plausible explanation of the most likely reaction mechanism, suggesting that the initial step is a 1,3-H shift with simultaneous ring opening. A 1-oxatrisulfane derivative formed thereby undergoes fragmentations via a radical and a competitive concerted pathway leading to the observed final products. The same mechanism also governs the thermal fragmentation of di-tert-butyl disulfide S-oxide. Its pyrolysis at 700 °C affords an analogous set of products, including the 1-oxatrisulfan-3-yl radical (HOSS·) as the key intermediate. 3,3,5,5-Tetramethyl-1,2,4-trithiolane 1-oxide was pyrolyzed in vacuo (FVP) yielding the 1-oxotrisulfan-1-yl radical, which was isolated in an Ar matrix at 10 K and subsequently characterized by spectroscopic methods (IR and UV/Vis). The same radical was obtained after vacuum pyrolysis of di-tert-butyl disulfide S-oxide.

π-Face-selective hetero Diels-Alder reactions of 3,4-di-tert-butylthiophene 1-oxide. An excellent trapping reagent for thioaldehydes and thioketones

Hetero Diels-Alder reactions of 3,4-di-tert-butylthiophene 1-oxide (1) with thioaldehydes and thioketones take place exclusively, except the reaction with thiobenzophenone, at the syn-π-face of 1 with respect to the S=O bond. The π-face selectivity was ex