8-Mercaptoquinoline

Base Information

• Chemical Name: 8-Mercaptoquinoline
• CAS No.: 491-33-8
• Molecular Formula: C9H7NS
• Molecular Weight: 161.227
• Hs Code.: 2933499090
• NSC Number: 48888
• UNII: F77S9F93J4
• DSSTox Substance ID: DTXSID70197678
• Nikkaji Number: J6.054B
• Wikipedia: 8-Mercaptoquinoline
• Wikidata: Q25323974
• ChEMBL ID: CHEMBL4076575
• Mol file: 491-33-8.mol

Synonyms:8-mercaptoquinoline;8-mercaptoquinoline hydrochloride;8-MQ;8-quinolinethiol;quinoline-8-thiol;sodium quinolinethiolate;SQT-8

Chemical Property of 8-Mercaptoquinoline

Chemical Property:

• Vapor Pressure: 0.00163mmHg at 25°C
• Boiling Point: 303.8°Cat760mmHg
• Flash Point: 137.5°C
• PSA: 51.69000
• Density: 1.246g/cm³
• LogP: 2.52350
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 161.02992040
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

Quinoline-8-thiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)S)N=CC=C2
• Uses: Quinoline-8-thiol is used as a reactant in the preparation of classical and nonclassical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates and as antitumor agents.

Technology Process of 8-Mercaptoquinoline

There total 4 articles about 8-Mercaptoquinoline 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: 75.0%

quinoline-8-sulfonyl chloride (18704-37-5) → 8-mercaptoquinoline (491-33-8)

Guidance literature:

With triphenylphosphine; In toluene; for 0.166667h; chemoselective reaction; Inert atmosphere;

DOI:10.1055/s-0029-1216955

Reference yield: 20.0%

8-bromoquinoline (16567-18-3) → 8-mercaptoquinoline (491-33-8)

Guidance literature:

With n-butyllithium; hydrogen sulfide; In diethyl ether; ethyl acetate; benzene;

Reference yield:

→ 8-mercaptoquinoline (491-33-8)

Guidance literature:

With hydrogenchloride; tin(ll) chloride;

upstream raw materials:

8-bromoquinoline

quinoline-8-sulfonyl chloride

Downstream raw materials:

Os(H)(CO)(SC₉H₆N)(P(C₆H₅)3)2

(5R,6R)-6-Ethyl-7-oxo-3-(quinolin-8-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

2-(quinolin-8-ylthio)acetic acid

Refernces

• 1、 Zajdel, Pawel,Marciniec, Krzysztof,Maslankiewicz, Andrzej,Grychowska, Katarzyna,Satala, Grzegorz,Duszynska, Beata,Lenda, Tomasz,Siwek, Agata,Nowak, Gabriel,Partyka, Anna,Wrobel, Dagmara,Jastrzebska-Wiesek, Magdalena,Bojarski, Andrzej J.,Wesolowska, Anna,Pawlowski, MacIej. "Antidepressant and antipsychotic activity of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole targeting serotonin 5-HT 1A/5-HT2A/5-HT7 and dopamine D 2/D3 receptors". . p. 42 - 50. Retrieved 2013/04/23.
• 2、 Maslankiewicz, Andrzej,Marciniec, Krzysztof,Pawlowski, Maciej,Zajdel, Pawel. "From haloquinolines and halopyridines to quinoline- and pyridinesulfonyl chlorides and sulfonamides". . p. 1975 - 1990. Retrieved 2008/09/16.