21019-51-2

Basic information

• Product Name: (R)-4-CHLOROSTYRENE OXIDE
• Synonyms: (2R)-2α-(4-Chlorophenyl)oxirane;(R)-(4-Chlorophenyl)oxirane;(R)-(-)-1-Chloro-4-(epoxyethyl)benzene;(R)-4-CHLOROSTYRENE OXIDE;(R)-2-(4-Chlorophenyl)oxirane;(2R)-2-(4-Chlorophenyl)oxirane
• CAS NO: 21019-51-2
• Molecular Formula: C₈H₇ClO
• Molecular Weight: 154.59
• Product Categories: Aromatics;Chiral Reagents;Miscellaneous Reagents
• Mol File: 21019-51-2.mol
• Article Data: 107

Chemical Properties

• Boiling Point: 230.4 °C at 760 mmHg
• Appearance: /
• Density: 1.283 g/cm³
• CAS DataBase Reference: (R)-4-CHLOROSTYRENE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-CHLOROSTYRENE OXIDE(21019-51-2)
• EPA Substance Registry System: (R)-4-CHLOROSTYRENE OXIDE(21019-51-2)

Safety Data

• Hazardous Substances Data: 21019-51-2(Hazardous Substances Data)

Usage

Uses

(R)-2-(4-Chlorophenyl)oxirane (cas# 21019-51-2) is a compound useful in organic synthesis.

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 2788-86-5 4-Chlorostyrene oxide 
• 96-09-3 styrene oxide 
• 51-79-6 urethane 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 343239-89-4 (R)-2-(4-chlorophenyl)-2-hydroxyethyl methanesulfonate 
• 182621-75-6 (R)?2?bromo?1?(4′?chlorophenyl)ethanol 
• 152142-03-5 (1R)-1-(4-chlorophenyl)-1,2-ethanediol 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 85864-33-1 phenyl(2-pivaloylamidophenyl)methane 
• 65-85-0 benzoic acid 
• 124-38-9 carbon dioxide 
• 937-20-2 p-chlorophenacyl chloride 
• 6314-52-9 2-bromo-1-(4-chlorophenyl)ethanol 

Downstream Products

• 7477-64-7 (S)-1-(4-chlorophenyl)-1,2-ethanediol 
• 152142-03-5 (1R)-1-(4-chlorophenyl)-1,2-ethanediol 
• 890038-05-8 C₁₂H₁₈ClNO₂ 
• 128535-89-7 (S)-(+)-2-amino-1-(p-chlorophenyl)ethanol 
• 1097211-44-3 C₁₉H₂₂ClNO₃ 
• 1097210-75-7 C₂₂H₂₈ClNO₃ 
• 1097211-33-0 C₂₃H₃₀ClNO₃ 
• 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 

Relevant articles and documents

Asymmetric Syntheses of 3,4-Disubstituted Tetrahydroquinoline Derivatives Using (+)-Sparteine-mediated Electrophilic Substitution

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Manganese-substituted carbonic anhydrase as a new peroxidase

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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.