773-76-2

Basic information

• Product Name: 5,7-Dichloro-8-hydroxyquinoline
• Synonyms: 5,7-Dichlor-8-hydroxychinolin;5,7-Dichloro-8-hydroquinoline;5,7-Dichloro-8-hydroxyquinolin;5,7-Dichloro-8-oxychinolin;5,7-Dichloro-8-oxyquinoline;5,7-dichloro-8-quinolino;5,7-Dichlorooxine;5,7-Dichloroxine
• CAS NO: 773-76-2
• Molecular Formula: C9H5Cl2NO
• Molecular Weight: 214.05
• EINECS: 212-258-3
• Product Categories: Quinolines, Quinazolines and derivatives;Haloquinolines;Hydroxyquinolines;Quinolines;Building Blocks;C8 to C10;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;CINAZYN
• Mol File: 773-76-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 178-180 °C(lit.)
• Boiling Point: 305.47°C (rough estimate)
• Flash Point: 168.3 °C
• Appearance: Light beige/Fluffy Powder
• Density: 1.3320 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, H
• PKA: 2.30±0.30(Predicted)
• Stability: Light Sensitive
• Merck: 14,2175
• BRN: 153606
• CAS DataBase Reference: 5,7-Dichloro-8-hydroxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-Dichloro-8-hydroxyquinoline(773-76-2)
• EPA Substance Registry System: 5,7-Dichloro-8-hydroxyquinoline(773-76-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36-37/39-25-22
• WGK Germany: 3
• RTECS: VC5350000
• TSCA: Yes
• Hazardous Substances Data: 773-76-2(Hazardous Substances Data)

Usage

Uses

Chloroxine, is an impurity of Cioquinol, which is an antifungal and antiprotozoal drug.

Indications

Chloroxine (Capitrol) shampoo contains a synthetic antibacterial compound similar to the hydroxyquinoline compounds used in dermatology for many years.

Definition

ChEBI: Quinolin-8-ol in which the hydrogens at positions 5 and 7 have been substituted by chlorine. An synthetic antibacterial prepared by chlorination of quinolin-8-ol, it is used for the treatment of dandruff and seborrhoeic dermatitis of the scalp.

Brand name

Capitrol (Westwood- Squibb).

Purification Methods

Crystallise the dichloro-oxine from acetone/EtOH. [Beilstein 21 H 95.]

InChI:InChI=1/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

Upstream product

• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 1419402-06-4 5,7-dichloro-8-quinolinyl-β-D-glucopyranoside 
• 88005-20-3 tetrakis(5,7-dichloro-8-quinolinolato)thorium(IV) * 5,7-dichloro-8-quinolinol 
• 123-91-1 1,4-dioxane 
• 130-26-7 5-chloro-7-iodoquinolin-8-ol 
• 7732-18-5 water 
• 83-73-8 5,7-diiodo-8-hydroxyquinoline 
• 609-89-2 2,4-dichloro-6-nitrophenol 
• 56-81-5 glycerol 
• 687638-05-7 5,7,7-trichloro-7H-quinoline-8-one 
• 521-74-4 broxyquinoline 
• 148-24-3 8-quinolinol 

Downstream Products

• 49638-84-8 undec-10-enoic acid-(5,7-dichloro-[8]quinolyl ester) 
• 18193-10-7 benzoic acid-(5,7-dichloro-[8]quinolyl ester) 
• 84165-43-5 2-(5,7-Dichloro-quinolin-8-yloxy)-1-phenyl-ethanone 
• 59460-86-5 [Cu(5,7-Cl-8-HQ)₂] 
• 492-61-5 β-D-glucose 
• 130-16-5 5-Chloro-8-hydroxyquinoline 

Relevant articles and documents

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.

QUINOLINE DERIVATIVES

The invention relates to new quinoline derivatives which are active CLK-1 inhibitors. More specifically, the CLK-1 inhibitors of the invention are compounds of formula (A). The invention also relates to pharmaceutical compositions comprising such compounds and to methods for the prophylaxis and/or treatment of disorders or their associated symptoms for which the inhibition of CLK-1 is beneficial.