491-33-8

Basic information

• Product Name: 8-Mercaptoquinoline Hydrochloride
• Synonyms: 8-MERCAPTOQUINOLINE;8-Quinolinethiol;8-Metcaptoquinoline;8-Quinolylmercaptan;Thiooxine;Quinoline-8-thiol;Thiooxin;Aids110552
• CAS NO: 491-33-8
• Molecular Formula: C₉H₇NS
• Molecular Weight: 161.2236
• Mol File: 491-33-8.mol

Chemical Properties

• Boiling Point: 303.8°Cat760mmHg
• Flash Point: 137.5°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 0.00163mmHg at 25°C
• Refractive Index: 1.706
• CAS DataBase Reference: 8-Mercaptoquinoline Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Mercaptoquinoline Hydrochloride(491-33-8)
• EPA Substance Registry System: 8-Mercaptoquinoline Hydrochloride(491-33-8)

Safety Data

• Hazardous Substances Data: 491-33-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Mercaptoquinoline Hydrochloride is used as a reactant for the synthesis of various compounds with potential pharmaceutical applications. Its ability to form 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines makes it a valuable starting material in the development of new drugs.
Used in Antifolate and Antitumor Agents:
8-Mercaptoquinoline Hydrochloride is used as a key component in the preparation of antifolate and antitumor agents. These compounds have shown promise in the treatment of various types of cancer by inhibiting essential metabolic pathways in cancer cells, thereby disrupting their growth and proliferation.

Purification Methods

It is more convenient to make 8-mercaptoquinoline by reduction of the disulfide. [Nakamura & Sekido Talanta 17 515 1970.] The hydrochloride (see thiooxine hydrochloride below) is more stable. [Beilstein 21 III/IV 1197, 21/3 V 30.]

InChI:InChI=1/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

Upstream product

• 16567-18-3 8-bromoquinoline 
• 18704-37-5 quinoline-8-sulfonyl chloride 

Downstream Products

• 57479-11-5 (±)-8-(o-tolyl)quinoline 
• 122179-85-5 2-(quinolin-8-ylthio)acetic acid 
• 1426232-02-1 C₂₃H₂₆Cl₂N₄O₂S 
• 132370-09-3 11-(8-quinolinylsulfanyl)lupinane 
• 166942-42-3 Os(H)(CO)(SC₉H₆N)(P(C₆H₅)3)2 
• 128517-88-4 AuP(C₆H₅)3C₉NH₆S 
• 188342-10-1 Au₂(C₉NH₆S)[P(C₆H₅)3]2⁽¹⁺⁾*BF₄^(1-)=Au₂(C₉NH₆S)[P(C₆H₅)3]2BF₄ 
• 18704-37-5 quinoline-8-sulfonyl chloride 

Relevant articles and documents

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

A series of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole was synthesized to explore the influence of two structural features-replacement of ether/amide moiety with sulfonamide one, and localization of a sulfonamide group in the azine moiety. In contrast to aripiprazole, compound 33 (N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl) quinoline-7-sulfonamide) and 39 (N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl) butyl)isoquinoline-3-sulfonamide) displaying multireceptor 5-HT 1A/5-HT2A/5-HT7/D2/D3 profile, and behaving as 5-HT1A agonists, D2 partial agonists, and 5-HT2A/5-HT7 antagonists, produced significant antidepressant activity in FST in mice. On the other hand, their 4-isoquinolinyl analog 40 (N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl) isoquinoline-4-sulfonamide), with similar receptor binding and functional profile, additionally displayed remarkable antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice.

A simple, fast and chemoselective method for the preparation of arylthiols

An efficient and convenient method for the synthesis of arylthiols by reaction of sulfonyl chlorides with triphenylphosphine in toluene is reported.

From haloquinolines and halopyridines to quinoline- and pyridinesulfonyl chlorides and sulfonamides

The action of sodium methanethiolate (in boiling DMF) towards haloazines (i.e. chloro- or bromo-pyridines and quinolines) (1) (with halogen substituent in non-aza-activated position) causes sequentially halogen ipso-substitution to methylthioazines (2) and then S-demethylation to azinethiolates (3A), which were: i) subjected to S-methylation, ii) oxidized to diazinyl disulfides (4) and iii) oxidatively chlorinated to azinesulfonyl chlorides (5). α- and γ-pyridine- and quinolinesulfonyl chlorides (5a, 5c, 5d and 5f) were prepared by oxidative chlorination of respective disulfides (4) performed in conc. hydrochloric acid and characterized by 1H and 13C NMR spectra. All azinesulfonyl chlorides (5) were effectively converted to corresponding azinesulfonamides (6).

Aryl-8-azabicyclo [3.2.1] octanes for the treatment of depression

The present invention includes compounds of formula I wherein A, X, n, Ar1, and Ar2 are defined as set forth herein. These compounds may be used to treat depression. The invention also includes formulations containing these compounds, and methods for making and using compounds of this invention.