4-Chloro-5-cyano-2-hydroxybenzoic acid

Base Information

• Chemical Name: 4-Chloro-5-cyano-2-hydroxybenzoic acid
• CAS No.: 55488-82-9
• Molecular Formula: C8H4ClNO3
• Molecular Weight: 197.578
• DSSTox Substance ID: DTXSID001282904
• Mol file: 55488-82-9.mol

Synonyms:4-Chloro-5-cyano-2-hydroxybenzoic acid;55488-82-9;Benzoic acid, 4-chloro-5-cyano-2-hydroxy-;SCHEMBL10658354;DTXSID001282904

Chemical Property of 4-Chloro-5-cyano-2-hydroxybenzoic acid

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 196.9879707
• Heavy Atom Count: 13
• Complexity: 259

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1C(=O)O)O)Cl)C#N

Technology Process of 4-Chloro-5-cyano-2-hydroxybenzoic acid

There total 3 articles about 4-Chloro-5-cyano-2-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: 43.0%

ethyl 4-chloro-5-cyano-2-hydroxybenzoate (105290-53-7) → 4-Chlor-5-cyan-salicylsaeure (55488-82-9)

Guidance literature:

With sodium hydroxide; at 50 - 60 ℃; for 9.5h;

DOI:10.1007/BF00816534

Reference yield:

4-amino-5-cyano-2-hydroxy-benzoic acid ethyl ester (72817-97-1) → 4-Chlor-5-cyan-salicylsaeure (55488-82-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaNO₂/H₂SO₄; 2.) CuCl/HCl conc. / 1.) glacial acetic acid, RT; 2.) 60 deg C - 70 deg C

2: 43 percent / 10 percent NaOH / 9.5 h / 50 - 60 °C

With hydrogenchloride; sodium hydroxide; sulfuric acid; copper(l) chloride; sodium nitrite;

DOI:10.1007/BF00816534

Reference yield:

→ 4-Chlor-5-cyan-salicylsaeure (55488-82-9)

Guidance literature:

5-Brom-4-chlorsalicylsaeuremethylester, CuCN;

upstream raw materials:

ethyl 4-chloro-5-cyano-2-hydroxybenzoate

4-amino-5-cyano-2-hydroxy-benzoic acid ethyl ester

Refernces

• 1、 Liebenow,Leuschner. "Structure activity relationship for derivatives of xipamide (4 chloro 5 sulfamoyl 2',6' salicyloxylidide)". . p. 240 - 244. Retrieved 2007/10/09.