115648-90-3

Basic information

• Product Name: (S)-3-CHLOROSTYRENE OXIDE
• Synonyms: (S)-3-CHLOROSTYRENE OXIDE;(S)-M-CHLOROSTYRENE OXIDE
• CAS NO: 115648-90-3
• Molecular Formula: C₈H₇ClO
• Molecular Weight: 154.59
• Mol File: 115648-90-3.mol

Chemical Properties

• Boiling Point: 229.4±28.0 °C(Predicted)
• Appearance: /
• Density: 1.283±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-3-CHLOROSTYRENE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-CHLOROSTYRENE OXIDE(115648-90-3)
• EPA Substance Registry System: (S)-3-CHLOROSTYRENE OXIDE(115648-90-3)

Safety Data

• Hazard Codes: F+
• RIDADR: cool dry tightly closed
• Hazardous Substances Data: 115648-90-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-3-CHLOROSTYRENE OXIDE is used as an epoxide reagent for various organic synthesis applications. Its unique chemical structure allows it to participate in a wide range of reactions, making it a valuable compound in the field of organic chemistry.
Used in Enzyme Cascades:
(S)-3-CHLOROSTYRENE OXIDE is used as an intermediate in the enzyme cascade involving the epoxidation-isomerization-amination of aryl-alkynes. This process is essential for the synthesis of various biologically active compounds, highlighting the importance of (S)-3-CHLOROSTYRENE OXIDE in the development of pharmaceuticals and other bioactive molecules.

Upstream product

• 2039-85-2 3-Chlorostyrene 
• 106262-93-5 (R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane 
• 117538-45-1 2-bromo-1-(3-chlorophenyl)ethanol 
• 106262-93-5 (+)-2-chloro-1-(3-chlorophenyl)ethanol 
• 185035-36-3 (R)-(-)-1-(3-chlorophenyl)-1,2-ethanediol-2-methanesulfonate 
• 20697-04-5 3-chlorostyrene oxide 
• 21886-56-6 3-chlorophenacyl chloride 
• 51-79-6 urethane 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 99-02-5 3'-Chloroacetophenone 
• 587-04-2 m-Chlorobenzaldehyde 
• 41011-01-2 2-bromo-1-(3-chloro-phenyl)-ethanone 
• 187409-10-5 3-chloro-α,β-dibromoethylbenzene 
• 873-63-2 m-chlorobenzyl alcohol 

Downstream Products

• 142796-55-2 (R)-1-(3-Chloro-phenyl)-2-[(R)-2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 136758-99-1 N-[(2(R) 7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]-(2R)-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride 
• 136759-00-7 N-[(2(S) 7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]-(2R)-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride 
• 185035-43-2 (R)-(-)-2-benzylamino-1-(3-chlorophenyl)ethanol 
• 80051-04-3 (R)-(-)-1-(3-chlorophenyl)-1,2-ethanediol 
• 454218-98-5 1(R)-(3-chloro-phenyl)-2-[1,1-dimethyl-2-(4-nitro-phenyl)-ethylamino]-ethanol 
• 699015-99-1 (1R)-1-(3-chlorophenyl)-2-{[(1R)-2-(4-iodophenyl)-1-methylethyl]amino}ethanol 
• 152358-49-1 C₁₉H₂₂ClNO₂ 
• 121216-31-7 N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(2R)-2-(3-chlorphenyl)-2-hydroxyethanamine 
• 639080-04-9 N-[2-(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indol-7-yloxy)acetyl]methanesulfonamide trifluoroacetate 
• 1241048-49-6 ethyl (1S,2R)-2-(3-chlorophenyl)-1-ethylcyclopropanecarboxylate 

Relevant articles and documents

Highly efficient asymmetric epoxidation of alkenes with a D4-symmetric chiral dichlororuthenium(IV) porphyrin catalyst

A dichlororuthenium(IV) complex of 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,2: 5,8-dimethanoanthrance-9-yl] porphyrin, [RuIV(D4-Por*)Cl2] (1), was prepared by heating [RuII-(D4-Po

Nonenzymatic Regeneration of Styrene Monooxygenase for Catalysis

Styrene monooxygenase (SMO) is a two-component flavoprotein catalyzing the selective epoxidation of various C=C double bonds. For cell-free catalysis, traditionally a cascade of NAD(P)H:flavin oxidoreductase, nicotinamide cofactor (NADH), and NADH regener

Stereo- and enantioselective alkene epoxidations: A comparative study of D4- and D2-symmetric homochiral trans-dioxoruthenium(VI) porphyrins

The mechanism of stoichiometric enantioselective alkene epoxidations by the D4- and D2-symmetric homochiral trans-dioxoruthenium(VI) porphyrins, [RuVI(D4-Por*)O2] (1) and [RuVI(D2-Por*)O2] (2a), in the presence of pyrazole (Hpz) was studied by UV/ Vis spectrophotometry and analysis of the organic products. The enantioselectivity of styrene oxidations is more susceptible to steric effects than to substituent electronic effects. Up to 72% ee was achieved for epoxidation of 3-substituted and cis-disubstituted styrenes by employing 1 as the oxidant, whereas entantioselectivities of only 20-40 % were obtained in the reactions with 2-substituted and trans-disubstituted styrenes. Complex 2a oxidized 2-substituted styrenes to their epoxides in up to 88% ee. Its reactions with transalkenes are more enantioselective (67 % ee) than with the cis-alkenes (40 % ee). Based on a two-dimensional NOESY NMR study, 2a was found to adopt a more open conformation in benzene than in dichloromethane, which explains the observed solvent-dependent enantioselectivity of its reactions with alkenes. The oxidation of aromatic alkenes by the chiral dioxoruthenium(VI) porphyrins proceeds through the ratelimiting formation of a benzylic radical intermediate; the observed enantioselectivity (eeobs) depends on both the facial selectivity of the first C-O bond formation step and the diastereoselectivity of the subsequent epoxide ring closure. To account for the observed facial selection, "side-on" and "top-on" approach transition state models are examined (see: B. D. Brandes, E. N. Jacobsen, Tetrahedron Lett. 1995, 36, 5123).

Coupling of biocatalytic asymmetric epoxidation with NADH regeneration in organic-aqueous emulsions

Cell-free enzymatic oxidations: Styrene monooxygenase (StyA) was used as a reagent for the gram-scale preparation of enantiopure epoxides. The catalyst is highly stable in a biphasic system and results in conversions of more than 88%. R1 = H, C

Enantioselective Epoxidation of Styrene Derivatives by Chloroperoxidase Catalysis

Chloroperoxidase catalysed epoxidation of styrene derivatives by t-BuOOH preferentially gives (R) oxides with ee values between 28 and 68percent.The data support the view of oxygen delivery from the ferryl oxygen directly to the substrate.

Styrene monooxygenase from Pseudomonas sp. LQ26 catalyzes the asymmetric epoxidation of both conjugated and unconjugated alkenes

A novel styrene monooxygenase (SMO) was isolated from Pseudomonas sp. LQ26, a styrene degrader from activated sludge. Sequence alignment demonstrated that it was the most distant member of all SMOs originating from the genus of Pseudomonas. The substrate spectrum of this enzyme extended beyond typical SMO substrates to 1-allylbenzene analogues, previously reported as non-substrates for the SMO from Pseudomonas fluorescens ST. The results demonstrate for the first time the asymmetric epoxidation of both conjugated and unconjugated alkenes catalyzed by SMO and suggest that a much broader substrate spectrum is expected for SMOs.

Direct electrochemical regeneration of monooxygenase subunits for biocatalylic asymmetric epoxidation

We report the first example of direct electrochemical regeneration of a flavin-dependent monooxygenase for asymmetric epoxidation catalysis. It is shown that electrochemical regeneration of the oxygenase subunit of the multicomponent styrene monooxygenase

Enantioselective epoxidation of terminal olefins by chiral dioxirane.

[see reaction]. This paper describes an enantioselective epoxidation of terminal olefins using chiral ketone 3 as catalyst and Oxone as oxidant. Up to 85% ee has been obtained.

Enantioselectivity of a recombinant epoxide hydrolase from Agrobacterium radiobacter

The recombinant epoxide hydrolase from Agrobacterium radiobacter AD1 was used to obtain enantiomerically pure epoxides by means of a kinetic resolution. Epoxides such as styrene oxide and various derivatives thereof and phenyl glycidyl ether were obtained in high enantiomeric excess and in reasonable yield. The enantioselectivity (E-value) of the resolution was calculated from progress curves for styrene oxide (E= 16.2) and para- chlorostyrene oxide (E=32.2).

Synthesis of enantiopure 3-chlorostyrene oxide via an asymmetric epoxidation-hydrolytic kinetic resolution sequence

3-Chlorostyrene oxide was prepared in >99% ee employing the (salen)Co- catalyzed hydrolytic kinetic resolution (HKR) reaction. The HKR was performed successfully on both racemic and enantiomerically enriched epoxides, the latter was obtained via (salen)Mn