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

• 100-42-5 styrene 
• 67-56-1 methanol 
• 108167-42-6 (-)-2-<(S)-N-(α-methylbenzyl)-N-benzylsulfamyl>-3-(pentafluorophenyl)oxaziridine 
• 96-09-3 styrene oxide 
• 1886-71-1 1,2-bis(tosyloxy)-1-phenylethane 
• 112009-61-7 (R)-1-chloro-2-hydroxy-3-phenylpropane 
• 70111-05-6 (S)-2-chloro-1-phenylethanol 
• 2425-28-7 (S)-2-bromo-1-phenylethanol 
• 42330-51-8 rac-(R)-1-phenyl-2-(p-tolylthio)ethan-1-ol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 100349-67-5 (1S)-2-iodo-1-phenylethanol 
• 14252-67-6 (S)-(+)-2-chloro-2-phenylethanol 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 17628-72-7 R-(-)-2-methoxy-2-phenyl ethanol 
• 116780-48-4 (R)-1-Adamantyl-2-phenylaziridine 
• 127811-26-1 (1R,4S)-4-Tetrahydropyranyloxy-1-phenyl-1-pentanol 
• 83541-27-9 N-<(S)-β-hydroxyphenethyl>valiolamine 
• 101540-71-0 N-<(R)-α-(hydroxymethyl)benzyl>valiolamine 
• 93-56-1 phenylethane 1,2-diol 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 60-12-8 2-phenylethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 74572-09-1 (S)-2-(2-hydroxy-ethylamino)-1-phenyl-ethanol 
• 477761-15-2 (S)-(+)-2-(tert-butylsulfanyl)-1-phenylethanol 
• 136581-87-8 (+)-(1S)-2-amino>1-phenylethanol 
• 16162-51-9 (S)-(-)-(2-hydroxy-2-phenyl-1-ethyl)-phenyl thioether 
• 116780-46-2 (R)-1-tert-Butyl-2-phenylaziridine 

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.

Structural and Biochemical Studies Enlighten the Unspecific Peroxygenase from Hypoxylon sp. EC38 as an Efficient Oxidative Biocatalyst

Unspecific peroxygenases (UPOs) are glycosylated fungal enzymes that can selectively oxidize C-H bonds. UPOs employ hydrogen peroxide as the oxygen donor and reductant. With such an easy-to-handle cosubstrate and without the need for a reducing agent, UPOs are emerging as convenient oxidative biocatalysts. Here, an unspecific peroxygenase from Hypoxylon sp. EC38 (HspUPO) was identified in an activity-based screen of six putative peroxygenase enzymes that were heterologously expressed in Pichia pastoris. The enzyme was found to tolerate selected organic solvents such as acetonitrile and acetone. HspUPO is a versatile catalyst performing various reactions, such as the oxidation of prim- and sec-alcohols, epoxidations, and hydroxylations. Semipreparative biotransformations were demonstrated for the nonenantioselective oxidation of racemic 1-phenylethanol rac-1b (TON = 13 000), giving the product with 88% isolated yield, and the oxidation of indole 6a to give indigo 6b (TON = 2800) with 98% isolated yield. HspUPO features a compact and rigid three-dimensional conformation that wraps around the heme and defines a funnel-shaped tunnel that leads to the heme iron from the protein surface. The tunnel extends along a distance of about 12 ? with a fairly constant diameter in its innermost segment. Its surface comprises both hydrophobic and hydrophilic groups for dealing with substrates of variable polarities. The structural investigation of several protein-ligand complexes revealed that the active site of HspUPO is accessible to molecules of varying bulkiness with minimal or no conformational changes, explaining the relatively broad substrate scope of the enzyme. With its convenient expression system, robust operational properties, relatively small size, well-defined structural features, and diverse reaction scope, HspUPO is an exploitable candidate for peroxygenase-based biocatalysis.

Construction of an Asymmetric Porphyrinic Zirconium Metal-Organic Framework through Ionic Postchiral Modification

Herein, one kind of neutral chiral zirconium metal-organic framework (Zr-MOF) was reported from the porphyrinic MOF (PMOF) family with a metallolinker (MnIII-porphyrin) as the achiral polytopic linker [free base tetrakis(4-carboxyphenyl)porphyrin] and chiral anions. Achiral Zr-MOF was chiralized through the exchange of primitive anions with new chiral organic anions (postsynthetic exchange). This chiral functional porphyrinic MOF (CPMOF) was characterized by several techniques such as powder X-ray diffraction, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1H NMR, energy-dispersive X-ray spectroscopy, scanning electron microscopy, and Brunauer-Emmett-Teller measurements. In the resulting structure, there are two active metal sites as Lewis acid centers (Zr and Mn) and chiral species as Br?nsted acid sites along with their cooperation as nucleophiles. This CPMOF shows considerable bimodal porosity with high surface area and stability. Additionally, its ability was investigated in asymmetric catalyses of prochiral substrates. Interactions between framework chiral species and prochiral substrates have large impacts on the catalytic ability and chirality induction. This chiral catalyst proceeded asymmetric epoxidation and CO2 fixation reactions at lower pressure with high enantioselectivity due to Lewis acids and chiral auxiliary nucleophiles without significant loss of activity up to the sixth step of consecutive cycles of reusability. Observations revealed that chiralization of Zr-MOF could happen by a succinct strategy that can be a convenient method to design chiral MOFs.