(2S)-2-(4-chlorophenyl)oxirane

Base Information

• Chemical Name: (2S)-2-(4-chlorophenyl)oxirane
• CAS No.: 97466-49-4
• Molecular Formula: C₈H₇ClO
• Molecular Weight: 154.596
• Hs Code.: 2910900090
• European Community (EC) Number: 821-471-6
• UNII: 659109YM0E
• DSSTox Substance ID: DTXSID60455310
• Nikkaji Number: J784.389E
• Wikidata: Q27263851
• Mol file: 97466-49-4.mol

Synonyms:(S)-2-(4-Chlorophenyl)oxirane;97466-49-4;(2S)-2-(4-chlorophenyl)oxirane;(s)-4-chlorostyrene oxide;(R)-2-(4-Chlorophenyl)oxirane;(2R)-2-(4-Chlorophenyl)oxirane;(S)-(4-Chlorophenyl)oxirane;4-Chlorostyrene oxide, (+)-;659109YM0E;Oxirane, 2-(4-chlorophenyl)-, (2S)-;4-Chlorostyrene oxide, (S)-;UNII-659109YM0E;(S)-p-Chlorostyrene oxide;(S)-para-chloro styrene oxide;SCHEMBL1022637;DTXSID60455310;IBWLXNDOMYKTAD-MRVPVSSYSA-N;(S)-2-(4-chloro-phenyl)-oxirane;AKOS006287744;AT32896;Oxirane,2-(4-chlorophenyl)-, (2S)-;(R)-(-)-1-Chloro-4-(epoxyethyl)benzene;CS-0183138;EN300-125232;Q27263851;Z1198173162

Chemical Property of (2S)-2-(4-chlorophenyl)oxirane

Chemical Property:

• Boiling Point: 229.409 °C at 760 mmHg
• Flash Point: 97.59 °C
• PSA: 12.53000
• Density: 1.284 g/cm³
• LogP: 2.41130
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.0185425
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-ChlorostyreneOxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)C2=CC=C(C=C2)Cl
• Isomeric SMILES: C1[C@@H](O1)C2=CC=C(C=C2)Cl
• Uses: (S)-4-Chlorostyrene oxide is used in the biosynthetic preparation though epoxidation of styrene and substituted styrenes by whole cells of Mycobacterium.

Technology Process of (2S)-2-(4-chlorophenyl)oxirane

There total 63 articles about (2S)-2-(4-chlorophenyl)oxirane 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: 96.0%

(S)-(+)-1-(4-Chlorophenyl)-2-(p-tolylsulfonyloxy)ethanol (357952-84-2) → (2S)-2-(4-chlorophenyl)oxirane (2788-86-5,21019-51-2,53649-47-1,97466-49-4)

Guidance literature:

With sodium hydroxide; In diethyl ether; at 20 ℃; for 3h;

DOI:10.1039/b010155i

Reference yield: 95.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) → (2S)-2-(4-chlorophenyl)oxirane (2788-86-5,21019-51-2,53649-47-1,97466-49-4)

Guidance literature:

With manganese(II) chloride tetrahydrate; iodosylbenzene; 5,10,15,20-tetrakis[(S)-3-benzyl-2-methyl-4-phenylbut-1-yl]porphyrin; In dichloromethane; at 20 ℃; for 2h; enantioselective reaction;

DOI:10.1142/S1088424616500620

Reference yield: 95.0%

(S)-1-acetoxy-2-bromo-1-(4-chlorophenyl)ethane → (2S)-2-(4-chlorophenyl)oxirane (2788-86-5,21019-51-2,53649-47-1,97466-49-4)

Guidance literature:

With lithium hydroxide; In ethanol; water; at 20 ℃; for 1h;

DOI:10.1039/c7ra00083a

upstream raw materials:

4-vinylbenzyl chloride

4-Chlorostyrene oxide

styrene oxide

urethane

Downstream raw materials:

(S)-1-(4-chlorophenyl)-1,2-ethanediol

(1R)-1-(4-chlorophenyl)-1,2-ethanediol

methyl 4-((7S)-7-{[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)benzoate

(7S)-7-{[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenol

Refernces

• 1、 Xiao, Hu,Dong, Shuang,Liu, Yan,Pei, Xiao-Qiong,Lin, Hui,Wu, Zhong-Liu. "A new clade of styrene monooxygenases for (R)-selective epoxidation". . p. 2195 - 2201. Retrieved 2021/04/12.
• 2、 Chao, Rebecca R.,Lau, Ian C.-K.,Coleman, Tom,Churchman, Luke R.,Child, Stella A.,Lee, Joel H. Z.,Bruning, John B.,De Voss, James J.,Bell, Stephen G.. "The Stereoselective Oxidation of para-Substituted Benzenes by a Cytochrome P450 Biocatalyst". . p. 14765 - 14777. Retrieved 2021/09/14.