1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane

Base Information

• Chemical Name: 1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane
• CAS No.: 56718-76-4
• Molecular Formula: C12H17ClO3
• Molecular Weight: 244.718
• Hs Code.: 2909490000
• European Community (EC) Number: 641-510-9
• UNII: 85325N238N
• Nikkaji Number: J2.395.559H
• Wikidata: Q27269579
• Mol file: 56718-76-4.mol

Synonyms:56718-76-4;1-Chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol;1-chloro-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol;rac 1-Chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propanol;1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane;Metoprolol IMpurity 13;UNII-85325N238N;2-Propanol, 1-chloro-3-(4-(2-methoxyethyl)phenoxy)-;(+/-)-1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane;85325N238N;SCHEMBL7215333;CS-O-31160;AS-83105;FT-0664758;F50553;A929300;EN300-10936047;1-Chloro-3-[4-(2-methoxyethyl)-phenoxy]propan-2-ol;1-Chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propanol;Q27269579;Z1606983719

Chemical Property of 1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane

Chemical Property:

• Vapor Pressure: 5.95E-06mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 364.5°C at 760 mmHg
• PKA: 13.12±0.20(Predicted)
• Flash Point: 174.2°C
• PSA: 38.69000
• Density: 1.157g/cm³
• LogP: 1.85400
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 244.0866221
• Heavy Atom Count: 16
• Complexity: 170

Purity/Quality:

98%Min ^*data from raw suppliers

rac1-Chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCC1=CC=C(C=C1)OCC(CCl)O
• Uses: An intermediate for the synthesis of -chlorohydrins and -chloroamines. An intermediate for the synthesis of β-chlorohydrins and β-chloroamines. An impurity found in metoprolol An intermediate for the synthesis of β-chlorohydrins and β-chloroamines. An impurity found in metoprolol. Metroprolol USP Related Compound B.

Technology Process of 1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane

There total 8 articles about 1-Chloro-2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)-propane 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%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol (56718-76-4)

Guidance literature:

With morpholine; 1,3,5-trichloro-2,4,6-triazine; In water; at 20 ℃; for 0.5h;

DOI:10.1002/hlca.200790008

Reference yield: 90.0%

4-(2-methoxyethyl)phenol (56718-71-9) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) + (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol (56718-76-4)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/j.bmcl.2003.09.070

Reference yield:

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol (56718-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol

2: H₂; AcOH / Pd/C

3: 10 percent / aq. NaOH

With sodium hydroxide; hydrogen; acetic acid; palladium on activated charcoal; In methanol;

DOI:10.1016/j.bmcl.2003.09.070

upstream raw materials:

4-(2-methoxyethyl)phenol

epichlorohydrin

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone

Downstream raw materials:

Acetic acid 1-chloromethyl-2-[4-(2-methoxy-ethyl)-phenoxy]-ethyl ester

(2S)-1-chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propyl stearate

Refernces

• 1、 Soni, Surbhi-,Dwivedee, Bharat P.,Sharma, Vishnu K.,Banerjee, Uttam C.. "Kinetic resolution of (: RS)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol: a metoprolol intermediate and its validation through homology model of Pseudomonas fluorescens lipase". . p. 36566 - 36574. Retrieved 2017/08/02.
• 2、 Regla, Ignacio,Luviano-Jardon, Axel,Demare, Patricia,Hong, Enrique,Torres-Gavilan, Alejandro,Lopez-Munguia, Agustin,Castillo, Edmundo. "Chemoenzymatic synthesis of the potential antihypertensive agent (2R,2′S)-β-hydroxyhomometoprolol". experimental part. p. 2439 - 2442. Retrieved 2009/04/11.