34008-94-1

Basic information

• Product Name: tert-butyl ethyl sulfone
• Synonyms: 2-(Ethylsulfonyl)-2-methylpropane; 2-(Ethylsulphonyl)-2-methylpropane; propane, 2-(ethylsulfonyl)-2-methyl-; tert-Butyl ethyl sulfone; tert-Butyl ethyl sulphone
• CAS NO: 34008-94-1
• Molecular Formula: C₆H₁₄O₂S
• Molecular Weight: 150.2392
• Mol File: 34008-94-1.mol

Chemical Properties

• Boiling Point: 247.6°C at 760 mmHg
• Flash Point: 105.1°C
• Density: 1.01g/cm³
• Vapor Pressure: 0.0399mmHg at 25°C
• Refractive Index: 1.433
• CAS DataBase Reference: tert-butyl ethyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl ethyl sulfone(34008-94-1)
• EPA Substance Registry System: tert-butyl ethyl sulfone(34008-94-1)

Safety Data

• Hazardous Substances Data: 34008-94-1(Hazardous Substances Data)

Upstream product

• 14290-92-7 2-(ethylthio)-2-methyl-propane 

Downstream Products

• 4866-54-0 (2-methyl-cyclopropyl)-benzene 
• 4866-54-0 cis-1-methyl-2-phenylcyclopropane 

Relevant articles and documents

Unusual Two-Bond 13C,13C Coupling Constants in Sulphones

A measurable coupling between carbon atoms through the SO2 group is observed in a series of structurally diverse sulphones.In open-chain (single coupling path) sulphones this 2J coupling ranges from 5.5 to 27.2 Hz, while in cyclic (multiple coupling path) sulphones values ranging from 4.3 to 21.6 Hz are observed.Sulphides and sulphoxides do not exhibit a corresponding coupling of comparable magnitude.A positive sign for this coupling is derived from the data of cyclic sulphones.Whereas substituents and branching at the coupling termini exert minor influences on the coupling, the most important factor determining the magnitude of the 2J(CSC) coupling is the hybridization of the coupling carbon atoms.A linear relationship between the 2J value and the s character product of the C-S bond forming C orbitals is established.KEY WORDS Sulphones 13C NMR Geminal 13C,13C coupling

Chemistry of peroxyacyl nitrates. Part III. The oxidation of thioethers by peroxyhexanoyl nitrate

The reaction of peroxyhexanoyl nitrate, 1a, a homologue of the atmospheric pollutant "PAN", 1b, with some twenty thioethers, is described.At 0-25 deg C, common thioethers such as Et2S or PhSMe are rapidly converted into sulfoxides in high yields in a variety of solvents, ranging from pentane and chloroform to acetic acid, methanol and aqueous acetonitrile.Rates are essentially solvent-independent, although the reaction is subject to marked steric hindrance.Relative rates for five p-substituted thioanisoles in MeOH at 22 deg C, leading to a Hammett ρ-value of -1.7, show that the sulfur atoms display nucleophilic character.Electron-attracting groups on α-carbon, such as in PhSCCl3 and in MeSCH2OC(O)Ph, inhibit the formation of sulfoxide.Addition of EtSH lowers the yield of sulfoxide, producing instead EtSSEt and EtSNO.Oxidation of Me2S by 1a with the NO2 group labelled by 18O does not give rise to 18O-enriched DMSO.Comparison of (CH3)2S with (CD3)2S revealed an inverse kinetic H/D isotope effect.The products obtained from 1a vary with solvent.In the presence of water or EtSH, hexanoic acid is formed, while methanol gives rise to methyl hexanoate, and in pentane/hexanoic acid, hexanoic anhydride is produced.In aprotic solvents, significant amounts of CO2 are formed.These observations can best be rationalized on the basis of an intermediate sulfurane R1R2S(ONO2)(OCOR), (I), produced from thioether R1SR2 and 1a, in the first step.The fate of (I) under various conditions is discussed.Finally, the features of the oxidation of thioethers by peroxyacylnitrate are compared with those of acyl peroxides and peroxy esters.It is suggested that in each case formation of a sulfurane may well be the first step.