141394-10-7

Basic information

• Product Name: Oxirane, (2-chlorophenyl)-, (2S)-
• CAS NO: 141394-10-7
• Molecular Formula: C8H7ClO
• Molecular Weight: 154.596
• Mol File: 141394-10-7.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: Oxirane, (2-chlorophenyl)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, (2-chlorophenyl)-, (2S)-(141394-10-7)
• EPA Substance Registry System: Oxirane, (2-chlorophenyl)-, (2S)-(141394-10-7)

Safety Data

• Hazardous Substances Data: 141394-10-7(Hazardous Substances Data)

Upstream product

• 2039-87-4 2-chlorostyrene 
• 62717-50-4 o-chlorostyrene oxide 
• 89-98-5 2-chloro-benzaldehyde 
• 32345-65-6 (DL)-o-chlorophenyl-1,2-ethanediol 
• 4209-25-0 2-chloro-1-(2-chlorophenyl)ethanone 
• 32345-65-6 (R)-(2-chlorophenyl)-1,2-ethanediol 

Downstream Products

• 1220251-83-1 2-[(2R)-2-(2-chlorophenyl)-2-hydroxyethyl]-1H-isoindole-1,3(2H)-dione 
• 29261-25-4 (-)-Isoprophenamine 
• 1323147-29-0 C₈H₆⁽²⁾HClO 

Relevant articles and documents

Microbiological transformations. Part 39: Determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: A theoretical analysis and a new method for its determination

In the course of this work we have devised new equations as well as a new method allowing for the total determination of the regioselectivity occurring during biohydrolysis of a racemic epoxide by an epoxide hydrolase. This determination is achievable by

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.

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.