911820-09-2

Basic information

• Product Name: Propanoic acid, 3-[(4-methylphenyl)sulfinyl]-, 1,1-dimethylethyl ester
• CAS NO: 911820-09-2
• Molecular Formula: C14H20O3S
• Molecular Weight: 268.377
• Mol File: 911820-09-2.mol

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 3-[(4-methylphenyl)sulfinyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 3-[(4-methylphenyl)sulfinyl]-, 1,1-dimethylethyl ester(911820-09-2)
• EPA Substance Registry System: Propanoic acid, 3-[(4-methylphenyl)sulfinyl]-, 1,1-dimethylethyl ester(911820-09-2)

Safety Data

• Hazardous Substances Data: 911820-09-2(Hazardous Substances Data)

Upstream product

• 106-45-6 para-thiocresol 
• 1663-39-4 tert-Butyl acrylate 
• 911820-17-2 3-[(4-methylphenyl)sulfanyl]propanoic acid tert-butyl ester 

Downstream Products

• 77944-42-4 (cyclopent-2-enyl)(p-tolyl)sulfoxide 
• 10381-71-2 p-tolyl allyl sulfoxide 
• 22865-49-2 4-methyl-4'-nitro-diphenyl sulphoxide 
• 20663-33-6 (S(S))-(+)-1-methoxy-3-(p-tolylsulfinyl)benzene 
• 960595-63-5 (R)-m-anisyl p-tolyl sulfoxide 
• 1669-18-7 (R)-p-methoxyphenyl-p-tolylsulfoxide 
• 21066-59-1 (S)-p-tolyl p-trifluoromethylphenyl sulfoxide 
• 10381-70-1 benzyl 4-methylphenyl sulfoxide 
• 1312161-87-7 1-methyl-3-((p-tolylsulfinyl)methyl)benzene 
• 1489228-66-1 1-methyl-2-((p-tolylsulfinyl)methyl)benzene 
• 1512843-66-1 1, 3-dimethyl-5-[(p-tolylsulfinyl)methyl]benzene 
• 17530-79-9 1-chloro-4-((p-tolylsulfinyl)methyl)benzene 
• 100716-17-4 1-bromo-4-((p-tolylsulfinyl)methyl)benzene 
• 1512843-67-2 1-(tert-butyl)-4-((p-tolylsulfinyl)methyl)benzene 

Relevant articles and documents

Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.

Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions generated in situ, via a retro-Michael reaction. The reaction takes place under metal-free and mild conditions. It is compatible with aryl, heteroaryl, and alkyl sulfoxides with up to 90% yield. This practical access to alkynyl sulfoxides is expected to facilitate the application of these useful building blocks in organic synthesis.

Nondirected Copper-Catalyzed Sulfoxidations of Benzylic C-H Bonds

A copper-catalyzed sulfoxidation of benzylic C-H bonds by nondirected oxidative C(sp3)-H activation was developed. The process proceeds via sulfenate anions, which are generated by base-triggered elimination of β-sulfinyl esters and benzyl radicals. The functional group tolerance is high, and the product yields are good.

Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a cinchona -derived phase-transfer reagent

Preliminary results concerning a conceptually novel route to chiral sulfoxides based on the asymmetric alkylation of sulfenate salts with alkyl halides mediated by a chiral phase-transfer catalyst are described. As a representative example, o-anisyl methyl sulfoxide was produced in 96% yield and with an enantiomeric excess of 58% using commercial cinchonidinium derivative 2a.

Preparation of allyl sulfoxides by palladium-catalyzed allylic alkylation of sulfenate anions

Palladium-catalyzed allylic alkylation of sulfenate anions, generated from β-sulfinylesters by retro-Michael reaction, can take place under biphasic conditions. This new reaction provides a simple, mild, and efficient route to allyl sulfoxides in good yields.