71902-32-4

Usage

Physical state

Colorless liquid.

Odor

Strong, sweet.

Usage in organic synthesis

Acts as a sulfide precursor and a reactant for the preparation of various thioethers.

Application in the food industry

Used as a flavoring agent.

Usage in perfumes and cosmetics

Serves as a fragrance ingredient.

Potential pharmaceutical applications

Synthesis of biologically active compounds.

Safety precautions

May cause skin and eye irritation upon contact; handle with caution.

Upstream product

• 67-56-1 methanol 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 1950-65-8 4-methoxybenzenesulfenyl chloride 

Relevant academic research and scientific papers

Hammett Correlations in the Photosensitized Oxidation of 4-Substituted Thioanisoles

Singlet oxygen is quenched by a series of 4-substituted thioanisoles (methoxy to nitro), with rate constant kt = 7 × 104 to 7 × 106 M-1 s-1, close to the value observed for the myoglobin-catalyzed sulfoxidation of the same sulfides. Correlations with σ (ρ = -1.97) and with Eox (slope -3.9 V-1) are evidence for an electrophilic mechanism. In methanol sulfoxides are formed (85%) via an intermediate quenched by diphenyl sulfoxide; competing minor paths lead to arylthiols, arylsulfenic acid, and aryl sulfoxides. In aprotic solvents, the sulfoxidation is quite sluggish, but carboxylic acids (mostly ≤0.1 M) enhance the rate by a factor of > 100. The protonated persulfoxide is formed in this case and acts as an electrophile with sulfides, again with a rate constant correlating with σ (ρ = -1.78).

Model Reaction of Self-Condensation of Sulfenic Acids. Kinetic Investigation for the Reaction of Methyl Benzenesulfenate with trans-Decalin-9-sulfenic Acid and 2-Methyl-2-propanesulfenic Acid

Reaction of 2-methyl-2-propanesulfenic acid (1) with methyl arenesulfenates (2) gave S-aryl 2-methyl-2-propanethiosulfinates quantitatively, and kinetic investigation was carried out.Second-order rate dependence (first-order in methyl benzenesulfenate (2a

CONCERNING THE MECHANISM OF THE FORMATION OF PHOSPHORANES FROM THE REACTION OF TRICOORDINATED PHOSPHORUS COMPOUNDS AND ALKYL BENZENESULFENATES

Trimethyl phosphite has been allowed to react with methyl benzenesulfenate, methyl p-methoxybenzenesulfenate, methyl m-trifluoromethylbenzenesulfenate and methyl p-nitrobenzenesulfenate.The first three esters react at virtually the same rate whereas the p-nitro compound is considerably less reactive.These data support a mechanism which involves direct insertion of phosphorus into the S-O bond with some donation of lone pairs on sulfur into an orbital on phosphorus in the transition state.Other experiments show that the reaction is irreversible.A dithioaryltrioxyphosphorane has been shown to decompose to a phosphite and a diaryl disulfide.