49639-26-1

Basic information

• Product Name: 1-phenyl-2-(phenylsulfinyl)ethanol
• Synonyms: 1-Phenyl-2-(phenylsulfinyl)ethanol
• CAS NO: 49639-26-1
• Molecular Formula: C₁₄H₁₄O₂S
• Molecular Weight: 246.3248
• Mol File: 49639-26-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 463.7°C at 760 mmHg
• Flash Point: 234.2°C
• Density: 1.28g/cm³
• Vapor Pressure: 2.14E-09mmHg at 25°C
• Refractive Index: 1.663
• CAS DataBase Reference: 1-phenyl-2-(phenylsulfinyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-2-(phenylsulfinyl)ethanol(49639-26-1)
• EPA Substance Registry System: 1-phenyl-2-(phenylsulfinyl)ethanol(49639-26-1)

Safety Data

• Hazardous Substances Data: 49639-26-1(Hazardous Substances Data)

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

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

Downstream Products

• 79157-37-2 1-phenyl-1-(3,4-dimethoxyphenyl)ethylene 
• 51003-88-4 1-(3,4-methylendioxyphenyl)-1-(phenyl)ethene 
• 24890-52-6 1-phenyl-1-(2,4-dimethoxyphenyl)ethylene 
• 141341-45-9 (2-methoxy-2-phenylethyl)(phenyl)sulfane 
• 442160-35-2 1-acetoxy-1-(2-naphthyl)-3-phenyl-2-(phenylsulfinyl)-2-propene 

Relevant articles and documents

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.

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.

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