52190-35-9

Basic information

• Product Name: 2-(METHYLTHIO)CYCLOHEXANONE
• Synonyms: 2-(METHYLTHIO)CYCLOHEXANONE;QFABNUVNDKOIEH-UHFFFAOYSA-N
• CAS NO: 52190-35-9
• Molecular Formula: C₇H₁₂OS
• Molecular Weight: 144.23
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 52190-35-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 45 °C10.1 mm Hg(lit.)
• Flash Point: 193 °F
• Appearance: /
• Density: 1.069 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.036mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• CAS DataBase Reference: 2-(METHYLTHIO)CYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(METHYLTHIO)CYCLOHEXANONE(52190-35-9)
• EPA Substance Registry System: 2-(METHYLTHIO)CYCLOHEXANONE(52190-35-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 52190-35-9(Hazardous Substances Data)

Usage

Organic compound

Yes

Common use

Synthetic intermediate in the production of various chemicals and pharmaceuticals

Appearance

Colorless to pale yellow liquid

Odor

Strong, pungent

Chemical reactivity

Ability to undergo oxidation, reduction, and substitution reactions

InChI:InChI=1/C7H12OS/c1-9-7-5-3-2-4-6(7)8/h7H,2-5H2,1H3

Upstream product

• 1056477-06-5 2-bromocyclohexanone 
• 5188-07-8 sodium thiomethoxide 
• 5813-48-9 Methanesulfenyl chloride 
• 108-94-1 cyclohexanone 
• 822-87-7 2-Chlorocyclohexanone 
• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 67-68-5 dimethyl sulfoxide 
• 5799-67-7 dimethyl(methylthio)sulfonium tetrafluoroborate 
• 110-83-8 cyclohexene 
• 542-18-7 cyclohexyl chloride 
• 56424-42-1 cyclohexylidene-(1-phenyl-ethyl)-amine 
• 74-93-1 methylthiol 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 

Downstream Products

• 53475-32-4 2-(o-tolylamino)cyclohex-2-enone 
• 154911-49-6 2-benzyl-2-(methylthio)cyclohexanone 
• 69263-03-2 2-methyl-2-(methylthio)cyclohexanone 
• 108920-21-4 trans-2-(methylsulfonyl)cyclohexanol 
• 108920-20-3 cis-2-(methylsulfonyl)cyclohexanol 
• 89729-99-7 2-(Hexylsulfonyl)-1-cyclohexanon 
• 89730-09-6 2-(3-Butenylsulfonyl)-1-cyclohexanon 
• 89730-08-5 2-(Nonylsulfonyl)cyclohexanon 
• 89730-00-7 2-(2-Phenylethylsulfonyl)-1-cyclohexanon 
• 85058-04-4 2-(Propylsulfonyl)-1-cyclohexanon 
• 154911-47-4 2-Butyl-2-methylthiocyclohexanone 
• 53475-33-5 2-((4-chlorophenyl)amino)cyclohex-2-en-1-one 
• 14755-90-9 2-Methylmercapto-cyclohexen-⁽²⁾-on 
• 16096-71-2 2-(Methylsulfonyl)-1-cyclohexanon 

Relevant articles and documents

Enantioselective Construction of Sulfur-Containing Tetrasubstituted Stereocenters via Asymmetric Functionalizations of α-Sulfanyl Cyclic Ketones

Asymmetric functionalizations of α-sulfanyl cyclic ketones were realized via chiral phosphoric acid catalyzed enantioselective addition reactions with aldimines, azodicarboxylates and allenamides. A series of chiral organosulfur compounds possessing sulfur-containing tetrasubstituted stereocenters were accessed via these methods, with excellent regioselectivities and high stereoselectivities. (Figure presented.).

RADIATION-SENSITIVE COMPOSITION OF CHEMICAL AMPLIFICATION TYPE

A chemically amplified radiation sensitive composition is provided which comprises a film forming hydroxystyrene based resin in combination with an onium salt precursor which generates a fluorinated alkanesulfonic acid as a photoacid generator. This composition can realize neither corrosion of apparatuses by outgas, nor T-shaped pattern profiles, nor change in linewidth attributable to process time delay, on the other side, high sensitivity and resolution, and good pattern profiles and stability thereof.

SYNTHESES DE CYCLOHEXENONES α-SUBSTITUEES VIA LA THERMOLYSE DE CETOSULFOXYDES TERTIAIRES

The sulfenylation-dehydrosulfenylation method, combined with carbon-carbon bond forming reactions, has been applied to the synthesis of some α-functionalized cyclohexenones 3.Hence, the sodium anion of the 2-methylthiocyclohexanone in THF reacts with primary, allyl and benzyl halides as well as with Michael acceptors to lead to the tertiary ketosulfides 1a-j.Further oxidation by NaIO4 and thermolysis in boiling toluene of the resulting sulfoxides 2 have been performed.The scope and limitations of this strategy are also discussed. Key Words: α-functionalized cyclohexenones; tertiary ketosulfides and ketosulfoxides; sulfenylation and deshydrosulfenylation; thermolysis.