(2R)-3-(4-chlorophenoxy)propane-1,2-diol

Base Information

• Chemical Name: (2R)-3-(4-chlorophenoxy)propane-1,2-diol
• CAS No.: 112652-61-6
• Molecular Formula: C9H11ClO3
• Molecular Weight: 202.638
• UNII: 471UZB51YK
• Nikkaji Number: J575.518B
• Wikidata: Q27126732
• Metabolomics Workbench ID: 60639
• Mol file: 112652-61-6.mol

Synonyms:(R)-chlorphenesin;Chlorphenesin, (R)-;471UZB51YK;(2R)-3-(4-chlorophenoxy)propane-1,2-diol;UNII-471UZB51YK;112652-61-6;(R)-glycerol alpha-p-chlorophenyl ether;(R)-p-chlorophenyl-alpha-glyceryl ether;(2R)-3-(4-chlorophenoxy)-1,2-propanediol;(2R)-3-(p-chlorophenoxy)-1,2-propanediol;(2R)-3-(p-chlorophenoxy)propane-1,2-diol;SCHEMBL21194;CHEBI:59479;PD132884;(r)-3-(4-chlorophenoxy)propane-1,2-diol;EN300-27115298;Q27126732;,2-PROPANEDIOL, 3-(4-CHLOROPHENOXY)-, (2R)-

Chemical Property of (2R)-3-(4-chlorophenoxy)propane-1,2-diol

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 202.0396719
• Heavy Atom Count: 13
• Complexity: 135

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1OCC(CO)O)Cl
• Isomeric SMILES: C1=CC(=CC=C1OC[C@@H](CO)O)Cl

Technology Process of (2R)-3-(4-chlorophenoxy)propane-1,2-diol

There total 15 articles about (2R)-3-(4-chlorophenoxy)propane-1,2-diol 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: 94.0%

4-chloro-phenol (106-48-9,82344-39-6) + (R)-oxiranemethanol (57044-25-4) → (R)-3-(4-chlorophenoxy)propane-1,2-diol (112652-61-6)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 80 ℃; for 18h;

DOI:10.1016/S0040-4020(99)00896-0

Reference yield: 48.0%

4-chlorophenyl 2,3-epoxypropyl ether (2212-05-7) → (R)-3-(4-chlorophenoxy)propane-1,2-diol (112652-61-6) + (S)-1,2-epoxy-3-(4-chlorophenoxy) propane (129098-57-3)

Guidance literature:

4-chlorophenyl 2,3-epoxypropyl ether; With C₅₇H₅₄CoN₃O₈; In dichloromethane; at 20 ℃; for 0.25h;

With water; In dichloromethane; at 20 ℃; for 6h; enantioselective reaction; Cooling with ice;

DOI:10.1002/adsc.201700788

Reference yield:

chlorphenesin (104-29-0) → (R)-3-(4-chlorophenoxy)propane-1,2-diol (112652-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / pyridine, DMAP / CH₂Cl₂

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, from -60 deg C to RT, 30 min

3: aq. sodium phosphate buffer, sucrose, baker's yeast / 2 h / Ambient temperature

With pyridine; dmap; baker's yeast; oxalyl dichloride; sodium phosphate buffer; dimethyl sulfoxide; triethylamine; Sucrose; In dichloromethane;

DOI:10.1016/S0957-4166(97)00626-5

upstream raw materials:

1-allyloxy-4-chlorobenzene

1-acetoxy-3-(4-chlorophenoxy)propan-2-ol

Acetic acid 1-acetoxymethyl-2-(4-chloro-phenoxy)-ethyl ester

1-acetoxy-3-(4-chlorophenoxy)propan-2-one

Downstream raw materials:

(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol