2-Chloro-6-methoxyphenol

Base Information

• Chemical Name: 2-Chloro-6-methoxyphenol
• CAS No.: 72403-03-3
• Molecular Formula: C7H7 Cl O2
• Molecular Weight: 158.584
• Hs Code.: 2909500000
• European Community (EC) Number: 879-141-2
• DSSTox Substance ID: DTXSID00222700
• Nikkaji Number: J114.463D
• Wikidata: Q83101020
• Mol file: 72403-03-3.mol

Synonyms:2-chloro-6-methoxyphenol;72403-03-3;Phenol, 2-chloro-6-methoxy-;chloroguaiacol;SCHEMBL4007444;DTXSID00222700;XCA40303;MFCD16998800;MB25402;DS-17875;CS-0197726;FT-0728903;EN300-111997;O10746;A1-20768

Chemical Property of 2-Chloro-6-methoxyphenol

Chemical Property:

• Vapor Pressure: 0.0878mmHg at 25°C
• Melting Point: 52.9 °C
• Boiling Point: 217.9°C at 760 mmHg
• PKA: 8.50±0.10(Predicted)
• Flash Point: 85.6°C
• PSA: 29.46000
• Density: 1.28g/cm³
• LogP: 2.05420
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 158.0134572
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

99%, ^*data from raw suppliers

2-Chloro-6-methoxyphenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=CC=C1)Cl)O

Technology Process of 2-Chloro-6-methoxyphenol

There total 9 articles about 2-Chloro-6-methoxyphenol 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: 87.2%

2-benzyloxy-3-chloroanisole (914454-80-1) → 2-methoxy-6-chlorophenol (72403-03-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1016/j.ejmech.2006.04.004

Reference yield: 44.0%

2-methoxy-phenol (90-05-1) → 4-Chloroguaiacol (16766-30-6) + 2-methoxy-6-chlorophenol (72403-03-3)

Guidance literature:

2-methoxy-phenol; With toluene-4-sulfonic acid; In water; acetonitrile; at 20 ℃; for 0.0833333h;

With N-chloro-succinimide; In water; acetonitrile; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1016/j.tet.2010.06.041

Reference yield:

2-benzyloxy-3-chlorophenyl acetate → 2-methoxy-6-chlorophenol (72403-03-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81.7 percent / aq. NaOH / methanol / 2 h / 20 °C

2: 67.6 percent / tetrabutylammonium bromide; aq. NaOH / CH₂Cl₂ / 7 h / 20 °C

3: 87.2 percent / hydrogen / Pd/C / methanol / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.ejmech.2006.04.004

upstream raw materials:

3-chloro-4-hydroxy-5-methoxybenzoic acid

3-Chlorocatechol

dimethyl sulfate

2-methoxy-phenol

Downstream raw materials:

(2-chloro-6-methoxy-phenoxy)-acetic acid

6-chloroguaiacol acetate

2-(2-chloro-6-methoxyphenoxy)ethylamine

N-[2-(2-chloro-6-methoxyphenoxy)ethyl]phthalimide

Refernces

• 1、 Vitaku, Edon,Njardarson, Jon T.. "A Mild meta-Selective C–H Alkylation of Catechol Mono-Ethers". supporting information. p. 3679 - 3683. Retrieved 2016/08/16.
• 2、 Pallavicini,Fumagalli,Gobbi,Bolchi,Colleoni,Moroni,Pedretti,Rusconi,Vistoli,Valoti. "QSAR study for?a?novel series of?ortho disubstituted phenoxy analogues of?α1-adrenoceptor antagonist WB4101". . p. 1025 - 1040. Retrieved 2007/10/03.