3-Chloro-5-hydroxybenzoic acid

Base Information

• Chemical Name: 3-Chloro-5-hydroxybenzoic acid
• CAS No.: 53984-36-4
• Molecular Formula: C7H5ClO3
• Molecular Weight: 172.568
• Hs Code.: 2918290000
• European Community (EC) Number: 803-932-3
• ChEMBL ID: CHEMBL2146910
• DSSTox Substance ID: DTXSID50517335
• Wikidata: Q72451775
• Mol file: 53984-36-4.mol

Synonyms:3-chloro-5-hydroxybenzoic acid

Chemical Property of 3-Chloro-5-hydroxybenzoic acid

Chemical Property:

• Melting Point: 244.0 to 248.0 °C
• Boiling Point: 364.805 °C at 760 mmHg
• PKA: 3.71±0.10(Predicted)
• Flash Point: 174.428 °C
• PSA: 57.53000
• Density: 1.536 g/cm³
• LogP: 1.74380
• Storage Temp.: room temp
• Solubility.: DMSO: soluble15mg/mL (clear solution)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 171.9927217
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Chloro-m-salicylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1O)Cl)C(=O)O
• Uses: 5-Chloro-m-salicylic Acid was studied as a potential selective lactate receptor (GPR81) agonists with antilipolytic effects. GPR81, also known as hydroxycarboxylic acid receptor 1 (HCAR1), is a recently de-orphanized receptor that is activated by lactic acid (EC50 ~ 1.5 mM) but not by other hydroxycarboxylic acids. 3-chloro-5-hydroxy Benzoic Acid (3-chloro-5-hydroxy BA) is an agonist of GPR81 (EC50 = 16 μM) that is inactive against the related GPR109a (HCAR2) receptor. It is similarly effective at GPR81 receptors from a variety of mammalian species and is bioavailable, stimulating lipolysis (increased serum free fatty acids) in mice fed high fat chow for 10 weeks. 3-chloro-5-hydroxy BA, like lactate, blocks basal ghrelin secretion by primary gastric mucosal cells.[Cayman Chemical]

Technology Process of 3-Chloro-5-hydroxybenzoic acid

There total 1 articles about 3-Chloro-5-hydroxybenzoic acid 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: 83.0%

3-chloro-5-methoxy-benzoic acid (82477-67-6) → 3-chloro-5-hydroxybenzoic acid (53984-36-4)

Guidance literature:

With aluminum oxide; iodine; tetra-(n-butyl)ammonium iodide; In toluene; for 4h; Heating / reflux;

Reference yield: 99.0%

methanol (67-56-1) + 3-chloro-5-hydroxybenzoic acid (53984-36-4) → methyl 3-chloro-5-hydroxybenzoate (98406-04-3)

Guidance literature:

With sulfuric acid; for 5.5h; Heating / reflux;

Reference yield: 75.0%

Chlorodifluoromethane (75-45-6) + 3-chloro-5-hydroxybenzoic acid (53984-36-4) → 3-chloro-5-difluoromethoxybenzoic acid (433926-80-8)

Guidance literature:

3-chloro-5-hydroxybenzoic acid; With sodium hydroxide; In chloroform; water;

Chlorodifluoromethane; In chloroform; water; at 20 ℃; for 2h;

upstream raw materials:

3-chloro-5-methoxy-benzoic acid

Downstream raw materials:

methyl 3-chloro-5-hydroxybenzoate

3-chloro-5-difluoromethoxybenzoic acid

3-(benzyloxy)-5-chlorobenzoic acid

Refernces

• 1、 -. "PHARMACEUTICAL COMBINATION". Page 55; 56. . Retrieved 2010/02/04.