85870-05-9

Basic information

• Product Name: 1-(4-methylphenylsulfonyl)propan-2-ol
• Synonyms: 1-(4-methylphenylsulfonyl)propan-2-ol
• CAS NO: 85870-05-9
• Molecular Weight: 214.285
• Mol File: 85870-05-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(4-methylphenylsulfonyl)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methylphenylsulfonyl)propan-2-ol(85870-05-9)
• EPA Substance Registry System: 1-(4-methylphenylsulfonyl)propan-2-ol(85870-05-9)

Safety Data

• Hazardous Substances Data: 85870-05-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(4-methylphenylsulfonyl)propan-2-ol is used as a reagent in the field of organic synthesis for its mild yet effective properties in facilitating a range of chemical reactions.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(4-methylphenylsulfonyl)propan-2-ol is utilized as a compound of interest for potential pharmacological and biological applications, given its unique structural features and reactivity.
Used in Chemical Research:
1-(4-methylphenylsulfonyl)propan-2-ol is also employed in the chemical research industry as a subject of study to understand its properties, reactivity, and possible applications in the development of new materials or processes.

Upstream product

• 3112-87-6 1-methyl-4-(prop-2-ene-1-sulfonyl)benzene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 75-56-9 methyloxirane 
• 91765-54-7 2-ethoxy-propyl p-tolyl sulphone 
• 5877-09-8 2-(4-methylphenylthio)-1-methylethanol 
• 75-07-0 acetaldehyde 
• 3185-99-7 Methyl p-tolyl sulfone 
• 98-59-9 p-toluenesulfonyl chloride 
• 32228-15-2 4-methylphenyl prop-1-enyl sulfone 
• 5366-49-4 4-toluenesulfonylacetone 
• 66623-35-6 1,2-Bis(4-methylphenylsulfonyl)propane 

Downstream Products

• 5366-49-4 4-toluenesulfonylacetone 
• 862249-95-4 acetic acid (R)-2-(4-methylphenyl)sulfonyl-1-methyl-ethyl ester 
• 106-48-9 4-chloro-phenol 

Relevant articles and documents

Efficient synthesis of an apremilast precursor and chiral β-hydroxy sulfones via ketoreductase-catalyzed asymmetric reduction

Ketoreductase (KRED)-catalyzed asymmetric reduction of prochiral ketones is an attractive method to synthesize chiral alcohols. Herein, two KREDs LfSDR1-V186A/E141I and CgKR1-F92I with complementary stereopreference were identified towards reduction of apremilast prochiral ketone intermediate 1a. LfSDR1-V186A/E141I exhibited >99% conversion and 99.2% ee yielding an apremilast chiral alcohol intermediate ((R)-2a) at 50 g L?1 substrate loading. Furthermore, we investigated the substrate scope of β-keto sulfones by using LfSDR1-V186A/E141I and CgKR1-F92I to produce both enantiomers of the corresponding β-hydroxy sulfones, with good-to-excellent conversion (up to >99%) and enantioselectivity (up to 99.9% ee) being obtained in most cases. Finally, the gram-scale synthesis of (R)-2a was performed by employing the crude enzyme of LfSDR1-V186A/E141I and BsGDH to afford the desired enantiomer with >99% conversion, 85.9% isolated yield and 99.2% ee. This study presents a biocatalytic strategy to synthesize chiral β-hydroxy sulfones.

Synthesis of β-hydroxy sulfones via opening of hydrophilic epoxides with zinc sulfinates in aqueous media

Reaction of hydrophilic epoxides (ethylene oxide and propylene oxide) with readily accessible zinc sulfinates in aqueous solution under essentially neutral conditions afforded β-hydroxy sulfones in good yields. This method avoids the need for organic solvents and produces ZnO as the only major reaction byproduct. 2-(Methylsulfonyl)ethanol, a common reagent for the protection of various functional groups, was obtained by this methodology from ethylene oxide in 78% yield. Reaction of various simple zinc alkane- and benzenesulfinates with propylene oxide proceeded regioselectively in 63-67% yield. The corresponding opening of these epoxides with zinc 1,3-butadiene-1-sulfinate afforded 1-butadienyl β-hydroxyalkyl sulfones in 30% yield. Mechanistic studies revealed that the yields of these products were limited by their consumption in competing intra- and intermolecular Michael addition processes.

Lipase-promoted dynamic kinetic resolution of racemic β-hydroxyalkyl sulfones

A series of racemic aryl β-hydroxyalkyl sulfones have been successfully transformed into the corresponding optically active O-acetyl derivatives in high yields (up to 80%) with enantiomeric excesses more than 99% using a dynamic kinetic resolution procedure, in which a lipase-promoted kinetic resolution is combined with a concomitant ruthenium-catalysed racemization of the substrates.

Diastereoselective oxidation of β-hydroxysulfides with TBHP: A comparative study of titanocenes and Ti(Oi-Pr)4 as catalysts

Titanocene dichlorides and Ti(Oi-Pr)4 have been used as catalysts for the oxidation with t-butyl hydroperoxide of racemic β-hydroxysulfides having a stereogenic carbon centre in α- or β- position with respect to the sulfur atom. β-Hydroxysulfides were oxidized in high yields to the corresponding sulfoxides, titanocenes being more chemo- and generally more diastereoselective than Ti(Oi-Pr)4. A divergent stereochemical outcome has been observed when using titanocenes or Ti(Oi-Pr)4 in the oxidation of protected β-hydroxy sulfides.

Sulfone Directed Rhodium Catalysed Hydroboration: Regiochemistry in Acyclic System

Rhodium catalysed hydroboration of allyl sulfones gave rise to Markownikoff product with high regioselectivity.

SULFINATES AS NUCLEOPHILES FOR THE RING-OPENING OF EPOXIDES: A CONVENIENT ROUTE TO β-HYDROXYSULFONES

It has been found that the nucleophilic ring-opening of epoxides by arenesulfinates, in the presence of magnmesium nitrate as a Lewis acid catalyst, provides a preparatively useful, convenient route to β-hydroxysulfones.