826-07-3

Basic information

• Product Name: thioanisole-α,α,α-d3
• Synonyms: thioanisole-α,α,α-d3
• CAS NO: 826-07-3
• Molecular Weight: 127.183
• Mol File: 826-07-3.mol

Chemical Properties

• CAS DataBase Reference: thioanisole-α,α,α-d3(CAS DataBase Reference)
• NIST Chemistry Reference: thioanisole-α,α,α-d3(826-07-3)
• EPA Substance Registry System: thioanisole-α,α,α-d3(826-07-3)

Safety Data

• Hazardous Substances Data: 826-07-3(Hazardous Substances Data)

Upstream product

• 1111-88-2 Trideutero-methylbromid 
• 930-69-8 sodium thiophenolate 
• 865-50-9 iodomethane-d3 
• 108-98-5 thiophenol 
• 811-98-3 d⁽⁴⁾-methanol 

Downstream Products

• 35449-57-1 ((methyl-d₃)sulfinyl)benzene 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 3112-85-4 methylphenylsulfonate 
• 14132-13-9 trideuteriomethanesulfonyl-benzene 
• 100-68-5 methyl-phenyl-thioether 

Relevant articles and documents

Mechanism of sulfone formation in the reaction of sulfides and singlet oxygen: Intermediacy of S-hydroperoxysulfonium ylide

H-D exchange was observed in the methyl group during the formation of sulfones in the reaction of dimethyl sulfide-d6 or thioanisole-α,α,α-d3 with singlet oxygen in aprotic solvents. No exchange was observed in the sulfoxides obtained. The proton in the sulfones was shown to come from adventitious water, since the oxidation of C6H5SCH3 in the presence of D2O lead to the formation of sulfones with monodeuteriation. The 16O2-18O2 tracer study demonstrated no oxygen scrambling in the sulfones. All the results indicate that the sulfones are formed intramolecularly via an intermediate possessing one activated proton exchangeable with trace water, a suggested structure for which is S-hydroperoxysulfonium ylides (RS+(OOH)CH2-). Kinetic isotope effects (k(H)/k(D) = 2-4) observed for methyl protons in the sulfone formation suggest that the rate-determining step is the intramolecular proton abstraction in the persulfoxides (RS+(OO-)CH3) generating S-hydroperoxysulfonium ylides. The conversion of the ylide intermediates to sulfones is shown to be facile on the basis of PM3 theoretical calculations.

Computational and Experimental Study of Turbo-Organomagnesium Amide Reagents: Cubane Aggregates as Reactive Intermediates in Pummerer Coupling

The dynamic equilibria of organomagnesium reagents are known to be very complex, and the relative reactivity of their components is poorly understood. Herein, a combination of DFT calculations and kinetic experiments is employed to investigate the detailed reaction mechanism of the Pummerer coupling between sulfoxides and turbo-organomagnesium amides. Among the various aggregates studied, unprecedented heterometallic open cubane structures are demonstrated to yield favorable barriers through a concerted anion-anion coupling/ S?O cleavage step. Beyond a structural curiosity, these results introduce open cubane organometallics as key reactive intermediates in turbo-organomagnesium amide mixtures.

Reaction of singlet oxygen with thioanisole in ionic liquids: A solvent induced mechanistic dichotomy

A study of the reaction of thioanisole with singlet oxygen in pyrrolidinium-and imidazolium-based ionic liquids has been carried out. In these solvents, thioanisole shows a strongly enhanced reactivity with respect to molecular aprotic solvents, probably

Ion-neutral complex formation and hydrogen-shifts in the alkene loss from ionized alkyl phenyl thioethers in the gas phase

The mechanistic aspects of alkene loss from ionized ethyl- and n-propyl phenyl thioethers have been studied by use of deuterium labelling and tandem mass spectrometry. Loss of ethene from the molecule ion of ethyl phenyl thioether proceeds predominantly b