49639-26-1

Usage

Structure

Phenyl group attached to a carbon atom, connected to a sulfinyl group and an ethyl group
The compound has a phenyl ring (a six-membered aromatic ring with hydrogen atoms) bonded to a carbon atom, which is further connected to a sulfinyl group (a sulfur atom double-bonded to an oxygen atom) and an ethyl group (a two-carbon chain with a hydrogen atom and a methyl group).

Chiral auxiliary

Used in organic synthesis
1-phenyl-2-(phenylsulfinyl)ethanol serves as a chiral auxiliary, which is a compound that helps induce chirality (the presence of non-superimposable mirror images, or enantiomers) in organic synthesis.

Precursor for enantiomerically pure compounds

Preparation of various compounds
As a chiral auxiliary, 1-phenyl-2-(phenylsulfinyl)ethanol acts as a starting material for the synthesis of enantiomerically pure compounds, which have a single, well-defined three-dimensional arrangement of atoms.

Reagent in asymmetric synthesis

Construction of chiral compounds
In asymmetric synthesis, 1-phenyl-2-(phenylsulfinyl)ethanol is used as a reagent to create chiral compounds, which have non-superimposable mirror images, by selectively favoring the formation of one enantiomer over the other.

Building block for pharmaceuticals and agrochemicals

Construction of complex molecules
The compound serves as a building block for the synthesis of more complex molecules, such as pharmaceuticals (drugs) and agrochemicals (chemicals used in agriculture), due to its versatile reactivity and structural features.

Potential applications in natural product synthesis

Synthesis of biologically active compounds
1-phenyl-2-(phenylsulfinyl)ethanol has potential applications in the synthesis of natural products, which are complex molecules found in nature with various biological activities, such as medicinal properties or pesticidal effects.

Upstream product

• 1193-82-4 racemic methyl phenyl sulfoxide 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 108-98-5 thiophenol 
• 67210-34-8 1-phenyl-2-phenylsulfanyl-ethanol 
• 96-09-3 styrene oxide 
• 10364-94-0 1-benzoylimidazole 
• 98-88-4 benzoyl chloride 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 70-11-1 α-bromoacetophenone 
• 6099-23-6 1-(phenylsulfinyl)acetophenone 

Downstream Products

• 67210-34-8 1-phenyl-2-phenylsulfanyl-ethanol 
• 6461-58-1 (1-chloro-2-(phenylsulfonyl)ethyl)benzene 
• 442160-22-7 1-acetoxy-1-phenyl-2-(phenylsulfinyl)ethane 
• 40110-66-5 (E)-2-phenyl-1-(phenylsulfinyl)ethene 
• 31552-02-0 (E)-penta-1,2,4-triene-1,5-diyldibenzene 
• 257904-77-1 2-(3-phenylpropa-1,2-dienyl)naphthalene 
• 442160-32-9 1,5-diphenyl-2-(phenylsulfinyl)-1-penten-3-ol 
• 442160-45-4 1,5-diphenyl-4-(phenylsulfinyl)-4-penten-1-yn-3-ol 
• 442160-33-0 3-acetoxy-1,5-diphenyl-2-(phenylsulfinyl)-1-pentene 
• 442160-46-5 3-acetoxy-1,5-diphenyl-4-(phenylsulfinyl)-4-penten-1-yne 
• 442160-34-1 1-(2-naphthyl)-3-phenyl-2-(phenylsulfinyl)-2-propen-1-ol 
• 442160-35-2 1-acetoxy-1-(2-naphthyl)-3-phenyl-2-(phenylsulfinyl)-2-propene 
• 141341-45-9 (2-methoxy-2-phenylethyl)(phenyl)sulfane 

Relevant academic research and scientific papers

Competition Between Cα-S and Cα-Cβ Bond Cleavage in β-Hydroxysulfoxides Cation Radicals Generated by Photoinduced Electron Transfer?

A kinetic and product study of the 3-cyano-N-methyl-quinolinium photoinduced monoelectronic oxidation of a series of β-hydroxysulfoxides has been carried out to investigate the competition between Cα-S and Cα-Cβ bond cleavage within the corresponding cation radicals. Laser flash photolysis experiments unequivocally established the formation of sulfoxide cation radicals showing their absorption band (λmax ≈ 520?nm) and that of 3-CN-NMQ? (λmax ≈ 390?nm). Steady-state photolysis experiments suggest that, in contrast to what previously observed for alkyl phenyl sulfoxide cation radicals that exclusively undergo Cα-S bond cleavage, the presence of a β-hydroxy group makes, in some cases, the Cα-Cβ scission competitive. The factors governing this competition seem to depend on the relative stability of the fragments formed from the two bond scissions. Substitution of the β-OH group with -OMe did not dramatically change the reactivity pattern of the cation radicals thus suggesting that the observed favorable effect of the hydroxy group on the Cα-Cβ bond cleavage mainly resides on its capability to stabilize the carbocation formed upon this scission.

Palladium-Catalyzed Reductive [5+1] Cycloaddition of 3-Acetoxy-1,4-enynes with CO: Access to Phenols Enabled by Hydrosilanes

A new palladium-catalyzed reductive [5+1] cycloaddition of 3-acetoxy-1,4-enynes with CO, enabled by hydrosilanes, has been developed for delivering valuable functionalized phenols. This methodology employs hydrosilanes as the external reagent to facilitate the [5+1] carbonylative benzannulation. The reaction is a conceptually and mechanistically novel carbonylative cycloaddition route for the construction of substituted phenols, through the formation of four new chemical bonds, with excellent functional-group tolerance.

Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides

An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. No special precautions are necessary to exclude oxygen, yet the products are formed without oxidation at the β-position. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.

Synthesis of 1,1-diarylethylenes

A facile route toward 1,1-diarylethylenes 6 has been developed in good yields via mCPBA-promoted oxidation of β-hydroxysulfides 2, BF3·OEt2-mediated Friedel-Crafts reaction of the resulting β-hydroxysulfoxides 3 with oxygenated benze

Br?nsted acid-catalyzed chemodivergent reactions of: Ortho -mercaptobenzyl alcohols with 3-alkyl-2-vinylindoles and styrenes: [5+2] cyclization versus hydroxysulfenylation

Chemodivergent [5+2] cyclization and hydroxysulfenylation reactions of ortho-mercaptobenzyl alcohols with 3-alkyl-2-vinylindoles and styrenes were established in the presence of Br?nsted acid, which provide efficient methods for constructing benzoxathiepi

Lithiated sulfoxides: α-Sulfinyl functionalized carbanions

Reactions of alkyl aryl sulfoxides H-CRR′S(O)Ar with n-BuLi-TMEDA (TMEDA = N,N,N′,N′-tetramethylethylenediamine) afforded α-sulfinyl functionalized alkyl aryl lithium compounds of the type [Li2{CRR′S(O)Ar}2(TMEDA)2] (1, R/

A novel rapid sulfoxidation of sulfides with cyclohexylidenebishydroperoxide

Cyclohexylidenebishydroperoxide was successfully used as the oxygen source for the oxidation of sulfides to sulfoxides for the first time. The sulfoxides were obtained in good to high yields without any detectable over-oxidation to sulfones under normal conditions.

Diastereoselective synthesis of β-hydroxy sulfoxides: Enzymatic and biomimetic approaches

Stereoselectivities of up to 98 % have been found in the enzymatic synthesis of β-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenase (CHMO). The diastereoselectivity of the "one-pot" preparation of the title compounds in the presence of bovine se

Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin: Scope and Chemoselectivity

The oxidation of sulfides with H2O2 catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03-0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90-95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25% of that of the substrate, sulfones are obtained in almost quantitative yield and with the same high chemoselectivity observed in the synthesis of sulfoxides.

A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide-metal exchange as the key reaction and an application to a total synthesis of male bean weevil sex attractant

The sulfoxide-metal exchange reaction of β-acetoxy sulfoxides or β-mesyloxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with a Grignard reagent or alkyllithium at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-substituted ethenyl p-tolyl sulfoxides. A synthesis of (-)-methyl (E)-2,4,5-tetradecatrienoate, a male bean weevil sex attractant, was realized by this method.