Benzenecarbothioic acid, 2-chloro-, S-phenyl ester

Base Information

• Chemical Name: Benzenecarbothioic acid, 2-chloro-, S-phenyl ester
• CAS No.: 21122-36-1
• Molecular Formula: C13H9ClOS
• Molecular Weight: 248.733
• DSSTox Substance ID: DTXSID90356841
• Nikkaji Number: J239.038H
• Wikidata: Q82136443
• Mol file: 21122-36-1.mol

Synonyms:S-phenyl o-chlorothiobenzoate;Benzenecarbothioic acid, 2-chloro-, S-phenyl ester;21122-36-1;DTXSID90356841;AKOS000672858;BRD-K00760325-001-01-0

Chemical Property of Benzenecarbothioic acid, 2-chloro-, S-phenyl ester

Chemical Property:

• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 248.0062638
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SC(=O)C2=CC=CC=C2Cl

Technology Process of Benzenecarbothioic acid, 2-chloro-, S-phenyl ester

There total 7 articles about Benzenecarbothioic acid, 2-chloro-, S-phenyl ester 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: 96.0%

thiophenol (108-98-5) + ortho-chlorobenzoic acid (118-91-2) → 2-Chlor-thiobenzoesaeure-S-phenylester (21122-36-1)

Guidance literature:

ortho-chlorobenzoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.166667h;

thiophenol; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1021/acs.orglett.9b00031

Reference yield: 92.0%

o-chlorobenzoyl chloride (609-65-4) + diphenyldisulfane (882-33-7) → 2-Chlor-thiobenzoesaeure-S-phenylester (21122-36-1)

Guidance literature:

With hydrogenchloride; zinc; In water; at 20 ℃; for 0.05h; Ionic liquid; Inert atmosphere;

DOI:10.1016/j.tet.2011.04.018

Reference yield: 90.0%

2-chloro-benzaldehyde (89-98-5) + thiophenol (108-98-5) → 2-Chlor-thiobenzoesaeure-S-phenylester (21122-36-1)

Guidance literature:

With dipotassium peroxodisulfate; tetraethylammonium bromide; In 1,2-dichloro-ethane; at 90 ℃; for 40h; Inert atmosphere;

DOI:10.1002/adsc.201300584

upstream raw materials:

o-chlorobenzoyl chloride

thiophenol

diphenyldisulfane

2-chloro-benzaldehyde

Downstream raw materials:

1-(2-chlorophenyl)-2-phenyl-1-ethanone

phenyl o-chlorobenzenedithiocarboxylate

2-chlorobenzanilide

Refernces

• 1、 Rong, Guangwei,Mao, Jincheng,Liu, Defu,Yan, Hong,Zheng, Yang,Chen, Jie. "Formation of C(sp2)-S bonds through decarboxylation of α-oxocarboxylic acids with disulfides or thiophenols". . p. 26461 - 26464. Retrieved 2015/03/30.
• 2、 Azeredo, Juliano B.,Godoi, Marcelo,Schwab, Ricardo S.,Botteselle, Giancarlo V.,Braga, Antonio L.. "Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation". supporting information. p. 5188 - 5194. Retrieved 2013/11/06.