97466-49-4

Basic information

• Product Name: (S)-3-CHLOROSTYRENE OXIDE
• Synonyms: (S)-3-CHLOROSTYRENE OXIDE;S-4-CHLOROSTYRENE OXIDE;(S)-M-CHLOROSTYRENE OXIDE;(S)-2-(4-Chlorophenyl)oxirane
• CAS NO: 97466-49-4
• Molecular Formula: C₈H₇ClO
• Molecular Weight: 154.59
• Product Categories: Chiral Reagent
• Mol File: 97466-49-4.mol
• Article Data: 107

Chemical Properties

• Boiling Point: 229.409 °C at 760 mmHg
• Flash Point: 97.59 °C
• Appearance: /
• Density: 1.284 g/cm³
• CAS DataBase Reference: (S)-3-CHLOROSTYRENE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-CHLOROSTYRENE OXIDE(97466-49-4)
• EPA Substance Registry System: (S)-3-CHLOROSTYRENE OXIDE(97466-49-4)

Safety Data

• Hazardous Substances Data: 97466-49-4(Hazardous Substances Data)

Usage

Uses

(S)-4-Chlorostyrene oxide is used in the biosynthetic preparation though epoxidation of styrene and substituted styrenes by whole cells of Mycobacterium.

Upstream product

• 536-38-9 4-chlorobenzoylmethyl bromide 
• 1073-67-2 4-vinylbenzyl chloride 
• 178460-78-1 (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol 
• 7477-64-7 (S)-1-(4-chlorophenyl)-1,2-ethanediol 
• 99-91-2 para-chloroacetophenone 
• 2788-86-5 4-Chlorostyrene oxide 
• 124-38-9 carbon dioxide 
• 6314-52-9 2-bromo-1-(4-chlorophenyl)ethanol 
• 65-85-0 benzoic acid 
• 85864-33-1 phenyl(2-pivaloylamidophenyl)methane 
• 104-88-1 4-chlorobenzaldehyde 
• 111324-03-9 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ⁵,4Λ⁵-catenadi(phosphazene) 
• 179065-35-1 (S)?2?bromo?1?(4′?chlorophenyl)ethanol 
• 937-20-2 p-chlorophenacyl chloride 

Downstream Products

• 603122-42-5 methyl 4-((7S)-7-{[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)benzoate 
• 603122-37-8 (7S)-7-{[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenol 
• 1048380-30-8 (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(phenylmethyl)amino]-1-ethanol 
• 1048380-35-3 (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)amino]-1-ethanol 
• 1048380-54-6 (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(phenyl)amino]-1-ethanol 
• 1048380-33-1 (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(methyl)amino]-1-ethanol hydrochloride 
• 3391-10-4 (R)-1-(4-chlorophenyl)ethan-1-ol 
• 1268337-06-9 (R)-2-azido-2-(4-chlorophenyl)ethan-1-ol 
• 297765-49-2 (S)-(+)-2-azido-1-(p-chlorophenyl)ethanol 
• 1304788-11-1 (S)-1-(4-chlorophenyl)-2-phenoxyethanol 
• 603122-44-7 sodium 4-((7S)-7-{[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)benzoate 
• 603123-38-2 C₃₁H₃₄ClNO₆ 
• 603123-54-2 C₃₁H₃₄ClNO₇ 
• 603123-68-8 5-[((7S)-7-{[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)oxy]-2-methoxybenzoic acid hydrochloride 

Relevant articles and documents

Enantiomer Separation of Nitriles and Epoxides by Crystallization with Chiral Organic Salts: Chirality Switching Modulated by Achiral Acids

Enantiomer separation of nitriles and epoxides by inclusion crystal formation with organic-salt type chiral hosts was achieved. The stereochemistry of the preferentially included nitrile could be switched only by changing the achiral carboxylic acid component. Crystallographic analysis of the inclusion crystals reveals that the hydrogen-bonding networks are controlled by the acidity of the phenol group of the acids, which results in chirality switching.

A new clade of styrene monooxygenases for (R)-selective epoxidation

Styrene monooxygenases (SMOs) are excellent enzymes for the production of (S)-enantiopure epoxides, but so far, only one (R)-selective SMO has been identified with a narrow substrate spectrum. Mining the NCBI non-redundant protein sequences returned a new distinct clade of (R)-selective SMOs. Among them,SeStyA fromStreptomyces exfoliatus,AaStyA fromAmycolatopsis albispora, andPbStyA fromPseudonocardiaceaewere carefully characterized and found to convert a spectrum of styrene analogues into the corresponding (R)-epoxides with up to >99% ee. Moreover, site 46 (AaStyA numbering) was identified as a critical residue that affects the enantioselectivity of SMOs. Phenylalanine at site 46 was required for the (R)-selective SMO to endow excellent enantioselectivity. The identification of new (R)-selective SMOs would add a valuable green alternative to the synthetic tool box for the synthesis of enantiopure (R)-epoxides.

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.