20288-49-7

Basic information

• Product Name: Benzene, 1-[(R)-butylsulfinyl]-4-methyl-
• CAS NO: 20288-49-7
• Molecular Formula: C11H16OS
• Molecular Weight: 196.313
• Mol File: 20288-49-7.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(R)-butylsulfinyl]-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(R)-butylsulfinyl]-4-methyl-(20288-49-7)
• EPA Substance Registry System: Benzene, 1-[(R)-butylsulfinyl]-4-methyl-(20288-49-7)

Safety Data

• Hazardous Substances Data: 20288-49-7(Hazardous Substances Data)

Upstream product

• 61187-72-2 (R)-(1-Butenyl)-p-tolyl-sulfoxid 
• 1889-20-9 n-butylmagnesium iodide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 693-04-9 butyl magnesium bromide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 1774-35-2 di(p-tolyl) sulfoxide 
• 1191-47-5 dibutylmagnesium 
• 443640-88-8 (S_S,S_S)-2-phenyl-1,1-di-p-tolylsulfinyl-ethylene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 109-72-8 n-butyllithium 
• 1307296-48-5 (R,S)-N-Benzyl-N-(1-phenylethyl)-p-toluenesulfinamide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 54828-68-1 (R)-p-tolyl vinyl sulfoxide 
• 59336-80-0 1,2-Dibrom-1-p-tolylsulfinylethan 

Downstream Products

• 100907-27-5 (S)-2-Methylene-4-p-tolylsulfanyl-heptanoic acid 
• 879881-82-0 (S)-2-Ethyl-3-(toluene-4-sulfonyl)-hexanoic acid benzylamide 
• 879881-77-3 (R)-5-Chloro-5-(toluene-4-sulfonyl)-octan-4-ol 
• 879881-79-5 (R)-5-Chloro-5-(toluene-4-sulfonyl)-octan-4-one 

Relevant articles and documents

Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases

We report on the development of high-throughput fluorogenic assay that can streamline directed evolution of enantioselective sulfoxide reductases. As a model, methionine sulfoxide reductase A (MsrA) has been evolved to expand its limited substrate scope. The resulting mutant MsrA can resolve a range of new challenging racemic sulfoxides with high efficiency including the pharmaceutically relevant albendazole sulfoxide. The simplicity and the level of throughput make this method also suitable for the screening of metagenomic libraries in future for the discovery of new enzymes with similar reactivities.

Intermolecular Pummerer Coupling with Carbon Nucleophiles in Non-Electrophilic Media

A new Pummerer-type C?C coupling protocol is introduced based on turbo-organomagnesium amides, which unlike traditional Pummerer reactions, does not require strong electrophilic activators, engages a broad range of C(sp3)-, C(sp2)-, and C(sp)-nucleophiles, and seamlessly integrates with C?H and C?X magnesiation. Given the central character of sulfur compounds in organic chemistry, this protocol allows access to unrelated carbonyls, olefins, organometallics, halides, and boronic esters through a single strategy.

Symmetric diarylsulfoxides as asymmetric sulfinylating reagents for dialkylmagnesium compounds

At -78 °C, primary dialkylmagnesium compounds reacted with diarylsulfoxides when 1.5 equiv of the dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide-magnesium exchanges (from the perspective of Ar2SO).