5324-56-1

Usage

Classification

Organic compound
Belongs to the class of benzene and substituted derivatives
Specifically belongs to phenylalcohols

Usage

Commonly used in the synthesis of pharmaceuticals and agrochemicals
Also used as a precursor in the production of other chemicals

Industry Applications

Potential applications in the fragrance and flavor industry
Aromatic properties
Utilized as a fragrance ingredient in cosmetics and personal care products

Intermediate

May be used as an intermediate in the production of various synthetic organic compounds

Upstream product

• 3708-04-1 2-methylsulfonyl-1-phenylethanone 
• 67-71-0 dimethylsulfone 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 67-68-5 dimethyl sulfoxide 
• 111613-52-6 (R)-2-methylthio-1-phenyl-ethanol 
• 65487-98-1 (S)-2-methylthio-1-phenyl-ethanol 
• 532-27-4 1-chloroacetophenone 
• 124-63-0 methanesulfonyl chloride 
• 536-74-3 phenylacetylene 
• 109183-66-6 (S)-2-phenyl-2-tetrahydropyranyloxy-1-p-toluenesulfonyloxyethane 
• 94199-20-9 (S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 
• 109183-66-6 (R)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethyl p-toluenesulfonate 
• 60168-63-0 (R)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 

Downstream Products

• 6038-47-7 (1-chloro-2-(methylsulfonyl)ethyl)benzene 
• 69263-12-3 4-phenyl-Δ^4a(8a)-2-thiaoctalin 2,2 dioxide 
• 15436-11-0 (E)-methyl styryl sulfone 
• 69263-11-2 2-(2-Methylsulfonyl-1-phenylaethyl)cyclohexanon 
• 344876-56-8 1-[6-(2-Methanesulfonyl-1-phenyl-ethyl)-cyclohex-1-enyl]-pyrrolidine 
• 69263-13-4 8a-α-hydroxy-4-β-phenyl-trans-2-thiadecalin 2,2 dioxide 
• 69263-13-4 8a-β-hydroxy-4-β-phenyl-cis-2-thiadecalin 2,2 dioxide 
• 5342-84-7 1-(methane-4-sulfonyl)-2-phenylethylene 
• 137390-66-0 (2S*,6R*)-2,6-diphenyl-1,4-oxathiane 4,4-dioxide 

Relevant academic research and scientific papers

Chemoenzymatic Oxosulfonylation-Bioreduction Sequence for the Stereoselective Synthesis of β-Hydroxy Sulfones

A series of optically active β-hydroxy sulfones has been obtained through an oxosulfonylation-stereoselective reduction sequence in aqueous medium. Firstly, β-keto sulfones were synthesized from arylacetylenes and sodium sulfinates to subsequently develop the carbonyl reduction in a highly selective fashion using alcohol dehydrogenases as biocatalysts. Optimization of the chemical oxosulfonylation reaction was investigated, finding inexpensive iron(III) chloride hexahydrate (FeCl3 ? 6H2O) as the catalyst of choice. The selection of isopropanol in the alcohol-water media resulted in high compatibility with the enzymatic process for enzyme cofactor recycling purposes, providing a straightforward access to both (R)- and (S)-β-hydroxy sulfones. The practical usefulness of this transformation was illustrated by describing the synthesis of a chiral intermediate of Apremilast. Interestingly, the development of a chemoenzymatic cascade approach avoided the isolation of β-keto sulfone intermediates, which allowed the preparation of chiral β-hydroxy sulfones in high conversion values (83–94 %) and excellent optical purities (94 to >99 % ee).

Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of α-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.

Efficient synthesis of chiral β-hydroxy sulfones: Via iridium-catalyzed hydrogenation

A highly efficient Ir/f-Amphol-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed to prepare a series of chiral β-hydroxy sulfones with good to excellent results (62%->99% conversions, 35%-99% yields and 86%->99% ee). Our Ir/f-Amphol L4 catalytic system exhibited very high activity; the gram-scale asymmetric hydrogenation was performed well with just 0.005 mol% catalyst loading (S/C = 20,000) to afford the desired product 2a with >99% conversion, 99% yield and 93% ee.

Iron-Catalyzed Synthesis of Sulfur-Containing Heterocycles

An iron-catalyzed synthesis of sulfur- and sulfone-containing heterocycles is reported. The method is based on the cyclization of readily available substrates and proceeded with high efficiency and diastereoselectivity. A variety of sulfur-containing heterocycles bearing moieties suitable for subsequent functionalization are prepared. Illustrative examples of such postcyclization modifications are also presented.

Synthesis of γ-sulfonyl δ-lactones and β-sulfonyl styrenes

A facile route to the synthesis of γ-sulfonyl lactones 5 and β-sulfonyl styrenes 6 has been developed, achieving moderate to good yields via the (1) NaH mediated Michael addition of β-ketosulfones 3 and methyl acrylate in refluxing THF and (2) NaBH4mediated stereoselective reduction/lactonization of δ-ketoesters 4 in boiling MeOH, or (3) boron trifluoride etherate mediated ring-opening of lactones 5 in MeOH at reflux.

Palladium-mediated synthesis of 1,1,2-triarylethanes. Application to the synthesis of CDP-840

A three-step protocol toward 1,1,2-triarylethanes 1 starting with β-ketosulfones 2 is developed. A facile process is carried out for the (1) reduction of 2 with NaBH4, (2) BF3·OEt2-mediated Friedel-Crafts reactions of the

Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones

A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group toler

Highly enantioselective one-pot synthesis of chiral β-hydroxy sulfones via asymmetric transfer hydrogenation in an aqueous medium

A mild transformation in an aqueous medium for the one-pot synthesis of optically active β-hydroxy sulfones is described. The intermediates of β-keto sulfones obtained via a nucleophilic substitution reaction of α-bromoketones and sodium sulfinates in Hs

Acid-promoted reaction of sulfonyl chlorides with alkenes: New approach to the regioselective synthesis of β-hydroxyl sulfone derivatives

Reaction of sulfonyl chlorides with alkenes and water in the presence of catalytic amount of sulfonic acid provided β-hydroxyl sulfone derivatives in high yields.

Asymmetric Radical Reaction in the Coordination Sphere. 2. Asymmetric Addition of Alkane- and Arenesulfonyl Chlorides to Olefins Catalyzed by a Ruthenium(II)-Phosphine Complex with Chiral Ligands

The addition of arenesulfonyl chlorides to styrene in the presence of a catalytic amount of a ruthenium(II) complex with chiral phosphine ligands, Ru2Cl43 or Ru2Cl43, proceeds under mild conditions to give optically active 1:1 adducts,