Methyl 4-chloro-3-hydroxybenzoate

Base Information

• Chemical Name: Methyl 4-chloro-3-hydroxybenzoate
• CAS No.: 166272-81-7
• Molecular Formula: C8H7ClO3
• Molecular Weight: 186.595
• Hs Code.: 2918290000
• DSSTox Substance ID: DTXSID00473735
• Wikidata: Q82303336
• Mol file: 166272-81-7.mol

Synonyms:Methyl 4-chloro-3-hydroxybenzoate;166272-81-7;4-CHLORO-3-HYDROXY-BENZOIC ACID METHYL ESTER;Methyl4-Chloro-3-hydroxybenzoate;MFCD11505968;4-Chloro-3-hydroxybenzoic Acid Methyl Ester;Benzoic acid, 4-chloro-3-hydroxy-, methyl ester;Methyl 4-chloro-3-hydroxy-benzoate;SCHEMBL560243;DTXSID00473735;JTYWGSFSTNIJTA-UHFFFAOYSA-N;AKOS006325459;AB64117;CS-W003784;FS-3726;SY023753;FT-0709607;EN300-1178559;A882338

Chemical Property of Methyl 4-chloro-3-hydroxybenzoate

Chemical Property:

• Melting Point: 100-101 °C
• Boiling Point: 288.3±20.0 °C(Predicted)
• PKA: 7.68±0.10(Predicted)
• PSA: 46.53000
• Density: 1.354±0.06 g/cm3(Predicted)
• LogP: 1.83220
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.0083718
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-3-hydroxybenzoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1)Cl)O
• Uses: 4-Chloro-3-hydroxybenzoic Acid Methyl Ester id used in the synthesis of antidepressants.

Technology Process of Methyl 4-chloro-3-hydroxybenzoate

There total 8 articles about Methyl 4-chloro-3-hydroxybenzoate 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: 92.0%

(2-chloro-5-(methoxycarbonyl)phenyl)boronic acid (913835-92-4) → 4-Chloro-3-hydroxy-benzoic acid methyl ester (166272-81-7)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; water; at 20 ℃;

Reference yield: 90.5%

methanol (67-56-1) + 2-chloro-5-(trifluoromethyl)phenol (40889-91-6) → 4-Chloro-3-hydroxy-benzoic acid methyl ester (166272-81-7)

Guidance literature:

2-chloro-5-(trifluoromethyl)phenol; With sulfuric acid; at 100 ℃; for 1h;

methanol; for 3h; Reflux;

DOI:10.1021/jm8007097

Reference yield: 90.0%

methanol (67-56-1) + 4-chloro-3-hydroxybenzoic acid (34113-69-4) → 4-Chloro-3-hydroxy-benzoic acid methyl ester (166272-81-7)

Guidance literature:

With hydrogenchloride; for 1h; Heating;

DOI:10.1248/cpb.42.2365

upstream raw materials:

methanol

4-chloro-3-hydroxybenzoic acid

2-chloro-5-(trifluoromethyl)phenol

(2-chloro-5-(methoxycarbonyl)phenyl)boronic acid

Downstream raw materials:

methyl 4-chloro-3-(2-formylphenoxy)benzoate

Methyl 4-chloro-3-(phenylmethoxy)benzoate

Refernces

• 1、 Fu, Ying,Wang, Kui,Wang, Peng,Zhao, Ze-Yu,Wang, Yun-Kai,Ye, Fei. "Synthesis and crystal structure of 5-chloro-3,4-dihydroxy-3-(2-hydroxyethyl) isobenzofuran-1(3H)-one". . p. 329 - 333. Retrieved 2018/09/29.
• 2、 Yang, Feipu,Jiang, Xiangrui,Li, Jianfeng,Wang, Yu,Liu, Yongjian,Bi, Minghao,Wu, Chunhui,Zhao, Qingjie,Chen, Weiming,Yin, Jingjing,Zhang, Jian,Xie, Yuanchao,Hu, Tianwen,Xu, Mingshuo,Guo, Shuang,Wang, Zhen,He, Yang,Shen, Jingshan. "Synthesis, structure-activity relationships, and biological evaluation of a series of benzamides as potential multireceptor antipsychotics". supporting information. p. 3141 - 3147. Retrieved 2016/06/13.