(S)-4-Bromostyrene oxide

Base Information

• Chemical Name: (S)-4-Bromostyrene oxide
• CAS No.: 148684-05-3
• Molecular Formula: C8H7BrO
• Molecular Weight: 199.047
• European Community (EC) Number: 855-355-1,855-360-9
• Nikkaji Number: J784.390I
• Mol file: 148684-05-3.mol

Synonyms:148684-05-3;(S)-4-Bromostyrene oxide;(2R)-2-(4-bromophenyl)oxirane;(S)-2-(4-Bromophenyl)oxirane;Oxirane, 2-(4-bromophenyl)-, (2S)-;(R)-2-(4-Bromophenyl)oxirane;(-)-(R)-4-BROMOSTYRENE OXIDE;SCHEMBL83447;NNINSLOEPXEZOZ-MRVPVSSYSA-N;(2S)-2-(4-bromophenyl) oxirane;AKOS017405181;CS-0132979;EN300-365871;Z1198177142

Chemical Property of (S)-4-Bromostyrene oxide

Chemical Property:

• PSA: 12.53000
• LogP: 2.52040
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 197.96803
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

98%Min ^*data from raw suppliers

Oxirane,2-(4-bromophenyl)-,(2S)- 96% ^*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)Br
• Isomeric SMILES: C1[C@@H](O1)C2=CC=C(C=C2)Br

Technology Process of (S)-4-Bromostyrene oxide

There total 26 articles about (S)-4-Bromostyrene 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%

(S)-1-acetoxy-2-bromo-1-(4-bromophenyl)ethane (117340-82-6) → 2-(4-bromophenyl)oxirane (148684-05-3)

Guidance literature:

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

DOI:10.1039/c7ra00083a

Reference yield: 87.0%

(2S,3S,SS)-3-(p-bromophenyl)-2-(p-tolylsulfinyl)oxirane (889132-63-2) → 2-(4-bromophenyl)oxirane (148684-05-3)

Guidance literature:

With methyllithium; In tetrahydrofuran; at -100 ℃; for 0.0166667h;

DOI:10.1055/s-2006-933131

Reference yield: 84.0%

1-bromo-4-ethenyl-benzene (2039-82-9) → 2-(4-bromophenyl)oxirane (148684-05-3)

Guidance literature:

With titanium(IV) isopropylate; C₅₀H₄₆N₂O₄; dihydrogen peroxide; In dichloromethane; water; at 20 ℃; for 9h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetasy.2010.01.023

upstream raw materials:

1-bromo-4-ethenyl-benzene

(+/-)-2-(4-bromophenyl)oxirane

(S)-2-(4-bromophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate

tert-butyl carbazate

Downstream raw materials:

C₁₄H₁₃BrO₂

p-bromophenylacetaldehyde

4-Bromophenethylamine

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

Refernces

• 1、 Hou, Xiao-Dong,Hu, Bo-Chun,Hu, Die,Lei, Yu-Qing,Rao, Yi-Jian,Wu, Min-Chen,Zhang, Dong. "Structure-Guided Regulation in the Enantioselectivity of an Epoxide Hydrolase to Produce Enantiomeric Monosubstituted Epoxides and Vicinal Diols via Kinetic Resolution". supporting information. p. 1757 - 1761. Retrieved 2022/03/16.
• 2、 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.