(S)-3-chlorostyrene oxide

Base Information

• Chemical Name: (S)-3-chlorostyrene oxide
• CAS No.: 115648-90-3
• Molecular Formula: C8H7 Cl O
• Molecular Weight: 154.596
• DSSTox Substance ID: DTXSID50466056
• Nikkaji Number: J1.043.679F
• Wikidata: Q82292443
• Mol file: 115648-90-3.mol

Synonyms:(S)-3-chlorostyrene oxide;115648-90-3;(S)-3-CHLOROSTYRENEOXIDE;Oxirane, (4-chlorophenyl)-, (2S)-;(2R)-2-(3-chlorophenyl)oxirane;(s)-2-(3-chlorophenyl)oxirane;SCHEMBL2080161;DTXSID50466056;YVMKRPGFBQGEBF-MRVPVSSYSA-N;(S)-(-)-3-Chlorostyrene Oxide;AKOS006274961;EN300-380213;OXIRANE,2-(3-CHLOROPHENYL)-, (2S)-

Chemical Property of (S)-3-chlorostyrene oxide

Chemical Property:

• Boiling Point: 229.4±28.0 °C(Predicted)
• PSA: 12.53000
• Density: 1.283±0.06 g/cm3(Predicted)
• LogP: 2.41130
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.0185425
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-(3-Chlorophenyl)oxirane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F+

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)C2=CC(=CC=C2)Cl
• Isomeric SMILES: C1[C@@H](O1)C2=CC(=CC=C2)Cl
• Uses: (S)-(3-Chlorophenyl)oxirane is an epoxide reagent used in orgnaic synthesis. An intermediate in the enzyme cascade involving the epoxidation-isomerization-amination of aryl-alkyenes.

Technology Process of (S)-3-chlorostyrene oxide

There total 69 articles about (S)-3-chlorostyrene oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

3-Chlorostyrene (2039-85-2,26100-04-9) → (R)-meta-chlorostyrene oxide (20697-04-5,53631-04-2,115648-90-3,62600-71-9)

Guidance literature:

With P₄₅₀tol-glucose dehydrogenase; In aq. phosphate buffer; ethanol; at 30 ℃; for 5h; enantioselective reaction; Microbiological reaction;

DOI:10.1039/c4cc03491k

Reference yield: 96.0%

(S)-2-chloro-1-(3-chlorophenyl)-ethanol (174699-78-6) → (S)-3-chlorostyrene oxide (115648-90-3)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2004.06.076

Reference yield: 95.0%

(R)-(-)-1-(3-chlorophenyl)-1,2-ethanediol-2-methanesulfonate (185035-36-3) → (R)-meta-chlorostyrene oxide (20697-04-5,53631-04-2,115648-90-3,62600-71-9)

Guidance literature:

With sodium hydroxide; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1080/00304940009356766

upstream raw materials:

3-Chlorostyrene

(R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane

2-bromo-1-(3-chlorophenyl)ethanol

(+)-2-chloro-1-(3-chlorophenyl)ethanol

Downstream raw materials:

(R)-1-(3-Chloro-phenyl)-2-[(R)-2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]-ethanol

N-[(2(R) 7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]-(2R)-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride

N-[(2(S) 7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]-(2R)-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride

(1 R)-2-{[2-(4-Aminophenyl)-1-methylethyl]amino}-1-(3-chlorophenyl)-1-ethanol

Refernces

• 1、 Paul, Caroline E.,Tischler, Dirk,Riedel, Anika,Heine, Thomas,Itoh, Nobuya,Hollmann, Frank. "Nonenzymatic Regeneration of Styrene Monooxygenase for Catalysis". . p. 2961 - 2965. Retrieved 2015.
• 2、 Hofstetter, Karin,Lutz, Jochen,Lang, Irene,Witholt, Bernard,Schmid, Andreas. "Coupling of biocatalytic asymmetric epoxidation with NADH regeneration in organic-aqueous emulsions". . p. 2163 - 2166. Retrieved 2004.
• 3、 Lin, Hui,Qiao, Jing,Liu, Yan,Wu, Zhong-Liu. "Styrene monooxygenase from Pseudomonas sp. LQ26 catalyzes the asymmetric epoxidation of both conjugated and unconjugated alkenes". . p. 236 - 241. Retrieved 2010.
• 4、 Tian,She,Xu,Shi. "Enantioselective epoxidation of terminal olefins by chiral dioxirane.". . p. 1929 - 1931. Retrieved 2001.
• 5、 Brandes, Bridget D.,Jacobsen, Eric N.. "Synthesis of enantiopure 3-chlorostyrene oxide via an asymmetric epoxidation-hydrolytic kinetic resolution sequence". . p. 3927 - 3933. Retrieved 1997.
• 6、 Jia, Xin,Wang, Zunsheng,Li, Zhi. "Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200". . p. 407 - 415. Retrieved 2008.
• 7、 Rose, Eric,Ren, Qi-Zhi,Andrioletti, Bruno. "A Unique Binaphthyl Strapped Iron-Porphyrin Catalyst for the Enantioselective Epoxidation of Terminal Olefins". . p. 224 - 230. Retrieved 2004.
• 8、 Sakthipriya, Pachiannan,Ananthi, Nallamuthu. "Asymmetric epoxidation of alkenes catalyzed by novel chiral porphyrin metal complexes". . p. 730 - 737. Retrieved 2016.
• 9、 Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu. "Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones". supporting information. p. 18039 - 18042. Retrieved 2021/11/16.
• 10、 Hirose, Takuji,Kodama, Koichi,Shimomura, Yuki. "Enantiomer Separation of Nitriles and Epoxides by Crystallization with Chiral Organic Salts: Chirality Switching Modulated by Achiral Acids". . p. 6552 - 6557. Retrieved 2021/11/16.