20780-54-5

Basic information

• Product Name: (S)-Styrene oxide
• Synonyms: (S)-(-)-Styrene oxide 98%, optical purity ee: 98% (HPLC);(epoxyethyl)-,(S)-Benzene;(S)-(-)-Epoxystyrene;(s)-benzen;(S)-(-)-1,2-EPOXYETHYLBENZENE;(S)-(+)-EPOXYETHYLBENZENE;(S)-EPOXYSTYROL;(S)-PHENYLETHYLENE OXIDE
• CAS NO: 20780-54-5
• Molecular Formula: C₈H₈O
• Molecular Weight: 120.15
• Product Categories: Chiral Compounds;Epoxides;chiral;Chiral Compound
• Mol File: 20780-54-5.mol
• Article Data: 264

Chemical Properties

• Boiling Point: 192-194 °C(lit.)
• Flash Point: 175 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.051 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.535
• Storage Temp.: 2-8°C
• BRN: 3587977
• CAS DataBase Reference: (S)-Styrene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Styrene oxide(20780-54-5)
• EPA Substance Registry System: (S)-Styrene oxide(20780-54-5)

Safety Data

• Hazard Codes: T
• Statements: 45-20/21-36/38
• Safety Statements: 53-26-36/37-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: CZ9625030
• F: 10
• Hazardous Substances Data: 20780-54-5(Hazardous Substances Data)

Usage

Description

(S)-Styrene oxide, also known as ChEBI, is the (S)-enantiomer of styrene oxide. It is a colorless to light yellow liquid and is an oxirane derivative. (S)-Styrene oxide is utilized as a monomer for the synthesis of polyesters with relatively high Tg values through ring-opening copolymerization. Additionally, it serves as a valuable intermediate in the preparation of levamisole, a nematocide and anticancer agent.

Uses

Used in Polymer Industry:
(S)-Styrene oxide is used as a monomer for the production of polyesters with relatively high Tg values. This application is due to its ability to undergo ring-opening copolymerization, which results in polyesters with enhanced properties.
Used in Pharmaceutical Industry:
(S)-Styrene oxide is used as an intermediate in the preparation of levamisole, a nematocide and anticancer agent. Its role in the pharmaceutical industry is crucial for the development of treatments for various types of cancer and parasitic infections.
Used in Chemical Industry:
(S)-Styrene oxide can undergo copolymerization with CO2 to form the corresponding polycarbonate in the presence of a cobalt-based catalyst system. This application is significant for the development of environmentally friendly and sustainable materials, as the use of CO2 as a feedstock reduces the carbon footprint of the process.

InChI:InChI=1/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2/t8-/m1/s1

Upstream product

• 2425-28-7 (S)-2-bromo-1-phenylethanol 
• 532-27-4 1-chloroacetophenone 
• 103590-74-5 (R)-(+)-2-chloro-2-phenethylacetic acid 
• 100-42-5 styrene 
• 96-09-3 styrene oxide 
• 103665-43-6 (S)-1-acetoxy-1-phenyl-2-chloroethane 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 17199-29-0 (S)-Mandelic acid 
• 1075-49-6 4-ethenylbenzoic acid 
• 50-99-7 D-glucose 
• 65-85-0 benzoic acid 
• 917-61-3 sodium isocyanate 
• 100-52-7 benzaldehyde 
• 104891-66-9 β-styrylchloromethyldimethylsilane 

Downstream Products

• 116780-48-4 (R)-1-Adamantyl-2-phenylaziridine 
• 116508-51-1 (1S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 2404-43-5 (2S)-2-methyl-2-phenyloxirane 
• 5689-12-3 1,1,3,3-tetramethylindane-2-one 
• 639011-12-4 (+)-(S)-2-(4-chloro-2-methylphenoxy)-1-phenylethanol 
• 639011-14-6 (+)-(S)-2-(4-chloro-2,6-dimethylphenoxy)-1-phenylethanol 
• 639011-08-8 (+)-(S)-2-(2-methylphenoxy)-1-phenylethanol 
• 639011-10-2 (+)-(S)-2-(4-chlorophenoxy)-1-phenylethanol 
• 14467-53-9 (S)-(+)-2-(-amino)-1-phenylethanol 
• 783368-21-8 tert-butyl cyclopropylmethyl-[(2S)-2-hydroxy-2-phenylethyl]carbamate 
• 111058-49-2 (S)-(+)-2-[4-(4-Fluorobenzoyl)-1-piperidyl]-1-phenylethanol 

Relevant articles and documents

Nature of the reaction intermediates in the flavin adenine dinucleotide-dependent epoxidation mechanism of styrene monooxygenase

Styrene monooxygenase (SMO) is a two-component flavoenzyme composed of anNADH-specific flavin reductase (SMOB) and FAD-specific styrene epoxidase (NSMOA). NSMOA binds tightly to reduced FAD and catalyzes the stereospecific addition of one atom of molecula

Systematic optimization of a biocatalytic two-liquid phase oxyfunctionalization process guided by ecological and economic assessment

Next to economic success, ecological considerations have become increasingly important for companies synthesizing various compounds ranging from bulk chemicals to pharmaceuticals. In this context, the economic and ecological feasibility of asymmetric biocatalytic styrene epoxidation has previously been investigated and compared to chemical alternatives. Although the biotechnological two-liquid phase approach was found to be highly interesting in economic terms, the ecological performance is restrained by the applied organic carrier solvent bis(2-ethylhexyl)phthalate, which is toxic to humans and produced from non-renewable resources. As an alternative carrier solvent, the biodiesel constituent ethyl oleate was tested. Furthermore, the switch from glucose to glycerol as a carbon and energy source was investigated, the latter being a cheap abundant resource, as it is a waste product of the biodiesel and soap industries. Both strategies slightly reduced the productivity and final product titer. An ecological and economic assessment on process level, however, revealed a superior environmental performance (by 13%) with ethyl oleate as the extractive solvent, at the expense of slightly reduced economics (by 9%), whereas glycerol use reduced the performance with respect to both aspects. Based on available data, the application of resting cells was evaluated, providing the opportunity of more efficient carbon utilization via decoupling of growth and biotransformation. Their stability is, however, yet to be improved to achieve competitiveness. In general, this study underlines the potential of ecological and economic assessments for systematic process intensification. Even if advantages of proposed changes seem obvious, their true suitability can only be judged by detailed economic and ecological analyses at the process level. The Royal Society of Chemistry 2012.

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.