Ethyl 5-chlorosalicylate

Base Information

• Chemical Name: Ethyl 5-chlorosalicylate
• CAS No.: 15196-83-5
• Molecular Formula: C9H9 Cl O3
• Molecular Weight: 200.622
• NSC Number: 203330
• DSSTox Substance ID: DTXSID60308377
• Wikidata: Q82056231
• Mol file: 15196-83-5.mol

Synonyms:15196-83-5;Ethyl 5-chlorosalicylate;ethyl 5-chloro-2-hydroxybenzoate;5-Chloro-2-hydroxybenzoic acid ethyl ester;5-Chlorosalicylic Acid Ethyl Ester;ethyl 5-chloro-salicylate;SCHEMBL3303821;DTXSID60308377;ATMSMRINTOGATK-UHFFFAOYSA-N;ethyl 2-hydroxy-5-chloro-benzoate;MFCD06204295;NSC203330;AKOS008952860;NSC-203330;CS-0209887;FT-0664960;D84516

Chemical Property of Ethyl 5-chlorosalicylate

Chemical Property:

• Vapor Pressure: 0.00283mmHg at 25°C
• Boiling Point: 276.5°C at 760 mmHg
• Flash Point: 121°C
• PSA: 46.53000
• Density: 1.3g/cm³
• LogP: 2.22230
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 200.0240218
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

97% ^*data from raw suppliers

5-ChlorosalicylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=CC(=C1)Cl)O
• Uses: 5-Chlorosalicylic Acid Ethyl Ester can be used as an intermediate in the preparation of quinoline derivatives as TGFβ inhibitors. Can be used as an intermediate in the preparation of quinoline derivatives as TGFβ inhibitors.

Technology Process of Ethyl 5-chlorosalicylate

There total 6 articles about Ethyl 5-chlorosalicylate 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: 88.0%

sulfuric acid (7664-93-9) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 5-chlorosalicylic acid ethyl ester (15196-83-5)

Guidance literature:

In ethanol; ethyl acetate;

Reference yield: 85.0%

ethanol (64-17-5) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 5-chlorosalicylic acid ethyl ester (15196-83-5)

Guidance literature:

With sulfuric acid; for 48h; Cooling with ice; Reflux;

DOI:10.1002/cmdc.202100559

Reference yield: 53.0%

3-chloro-benzoic acid ethyl ester (1128-76-3) → 5-chlorosalicylic acid ethyl ester (15196-83-5)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; Selectfluor; trifluoroacetic acid; trifluoroacetic anhydride; at 105 ℃; for 10h;

DOI:10.1021/ol301104n

upstream raw materials:

2-hydroxy-benzoic acid ethyl ester

sulfuric acid

5-chloro-2-hydroxybenzoic acid

ethanol

Downstream raw materials:

2-Carbamoyloxy-5-chloro-benzoic acid ethyl ester

chloro-5 α,α-diethyl hydroxy-2 benzene methanol

5-chlorosalicylhydrazide

ethyl 5-chloro-2-hydroxy-3-nitrobenzoate

Refernces

• 1、 Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu. "Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids". supporting information. p. 7443 - 7449. Retrieved 2020/10/09.
• 2、 Hadj-esfandiari, Narges,Navidpour, Latifeh,Shadnia, Hooman,Amini, Mohsen,Samadi, Nasrin,Faramarzi, Mohammad Ali,Shafiee, Abbas. "Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives". . p. 6354 - 6363. Retrieved 2008/09/21.