(R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE

Base Information

• Chemical Name: (R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE
• CAS No.: 129098-58-4
• Molecular Formula: C9H9ClO2
• Molecular Weight: 184.622
• Mol file: 129098-58-4.mol

Synonyms:

Chemical Property of (R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE

Chemical Property:

• PSA: 21.76000
• LogP: 2.11760

Purity/Quality:

99%min ^*data from raw suppliers

(2R)-2-[(4-Chlorophenoxy)methyl]oxirane 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE

There total 11 articles about (R)-2-((4-CHLOROPHENOXY)METHYL)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: 61.0%

4-chlorophenyl 2,3-epoxypropyl ether (2212-05-7) → (R)-2-((4-chlorophenoxy)methyl)oxirane (129098-58-4)

Guidance literature:

With (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino-cobalt(II); water; acetic acid; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm2003365

Reference yield: 45.63%

(R)-(-)-epichlorohydrin (51594-55-9,24969-06-0,13403-37-7) + 4-chloro-phenol (106-48-9,82344-39-6) → (R)-2-((4-chlorophenoxy)methyl)oxirane (129098-58-4)

Guidance literature:

4-chloro-phenol; With potassium carbonate; In butanone; at 20 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

(R)-(-)-epichlorohydrin; In butanone; at 90 ℃; for 15h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.bmcl.2012.12.072

Reference yield:

4-chlorophenyl 2,3-epoxypropyl ether (2212-05-7) → chlorphenesin (104-29-0) + (S)-1,2-epoxy-3-(4-chlorophenoxy) propane (129098-57-3) + (R)-2-((4-chlorophenoxy)methyl)oxirane (129098-58-4)

Guidance literature:

With Bacillus megaterium ECU₁₀₀₁ epoxide hydrolase; In potassium phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 0.5h; pH=7; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/adsc.201100031

upstream raw materials:

4-chlorophenyl 2,3-epoxypropyl ether

(S)-Glycidyl tosylate

4-chloro-phenol

(R)-(-)-epichlorohydrin

Downstream raw materials:

1-((S)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol

(R)-1-(((1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-chlorophenoxy)propan-2-ol

(R)-1-(tert-butylamino)-3-(4-chlorophenoxy)propan-2-ol

C₂₀H₂₅ClN₂O₃

Refernces

• 1、 Ema, Tadashi,Yokoyama, Maki,Watanabe, Sagiri,Sasaki, Sota,Ota, Hiromi,Takaishi, Kazuto. "Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide". supporting information. p. 4070 - 4073. Retrieved 2017/08/15.
• 2、 Cai, Yuanchun,Lian, Mingming,Li, Zhi,Meng, Qingwei. "Enantioselective α-hydroxylation of β-keto esters catalyzed by chiral S-timolol derivatives". experimental part. p. 7973 - 7977. Retrieved 2012/09/21.