7321-56-4

Usage

Physical state

Colorless liquid at room temperature

Odor

Strong, sweet

Usage

Flavoring agent in the food industry (found in garlic, onion, and mushrooms)

Industrial applications

Precursor in the production of pharmaceuticals and agrochemicals

Health properties

Antioxidant and anti-inflammatory

Potential applications

Treatment of certain diseases

Safety concerns

Flammable, may cause irritation if inhaled, ingested, or in contact with skin

Upstream product

• 676-85-7 methylsulphinyl chloride 
• 95-46-5 2-methylphenyl bromide 
• 67-68-5 dimethyl sulfoxide 
• 137-06-4 2-thiocresol 

Downstream Products

• 5285-88-1 1-methyl-2-thiocyanatobenzene 
• 158837-85-5 <(2-Methylphenyl)thio>acetic acid methyl ester 
• 107538-00-1 (S)-1-methyl-2-(methylsulfinyl)benzene 
• 84413-66-1 (R)-1-methyl-2-(methylsulfinyl)benzene 
• 14092-00-3 methyl o-tolyl sulfide 
• 1426131-94-3 1-((4-(tert-butyl)benzyl)sulfinyl)-2-methylbenzene 

Relevant academic research and scientific papers

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

Electrochemical synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide

A new route for a one-pot synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide using an electrochemical technique was developed. This protocol proceeded smoothly by employing electrons and hydrogen peroxide as clean oxidants, and a wide range of aromatic and aliphatic sulfoxides were synthesized in moderate to good yields.

Formation of Ternary Inclusion Crystal and Enantioseparation of Alkyl Aryl Sulfoxides by the Salt of Urea-Modified l -Phenylalanine and an Achiral Amine

Chiral supramolecular hosts comprising urea-modified l-phenylalanines and achiral primary amines were developed, which facilitated enantioselective inclusion of alkyl aryl sulfoxides (3) up to 89% ee owing to the formation of ternary inclusion crystals. F

Sulfoxide-to-sulfilimine conversions: Use of modified Burgess-type reagents

Sulfoxides can directly be converted into N-cyanosulfilimines using a new Burgess-type reagent. By applying this strategy with a related reagent variant, synthetically valuable NH-sulfoximines have been prepared from sulfoxides via N-protected sulfilimines. The practical three-step reaction sequence is generally high yielding and applicable to a wide range of substrates. The sulfoxide-to-sulfilimine conversion can also be performed under solvent-reduced conditions in a ball mill. Copyright