Chloroxine

Base Information

• Chemical Name: Chloroxine
• CAS No.: 773-76-2
• Molecular Formula: C9H5Cl2NO
• Molecular Weight: 214.051
• Hs Code.: 29334900
• European Community (EC) Number: 212-258-3
• NSC Number: 758398,3904
• UNII: 2I8BD50I8B
• DSSTox Substance ID: DTXSID5022801
• Nikkaji Number: J7.088B
• Wikipedia: Chloroxine
• Wikidata: Q12029435
• NCI Thesaurus Code: C47446
• Metabolomics Workbench ID: 43451
• ChEMBL ID: CHEMBL1200596
• Mol file: 773-76-2.mol

Synonyms:chloroxine;chloroxine hydrofluoride;chlorquinol;dichlorohydroxyquinoline;dichloroquine;quixalin

Chemical Property of Chloroxine

Chemical Property:

• Appearance/Colour: light beige fluffy powder
• Melting Point: 178-180 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 354.7 °C at 760 mmHg
• PKA: 2.30±0.30(Predicted)
• Flash Point: 168.3 °C
• PSA: 33.12000
• Density: 1.538 g/cm³
• LogP: 3.24720
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, H
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 212.9748192
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Chloroxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36-37/39-25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C(C=C2Cl)Cl)O)N=C1
• 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.

Technology Process of Chloroxine

There total 12 articles about Chloroxine 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: 98.4%

8-quinolinol (148-24-3,24804-14-6) → chloroxine (773-76-2)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; In acetonitrile; at 20 - 25 ℃; for 0.25h; Green chemistry;

DOI:10.1016/j.tetlet.2020.152689

Reference yield: 90.0%

broxyquinoline (521-74-4) → chloroxine (773-76-2)

Guidance literature:

With pyridine hydrochloride; at 220 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(96)01449-9

Reference yield: 71.0%

8-quinolinol (148-24-3,24804-14-6) → chloroxine (773-76-2) + 5-Chloro-8-hydroxyquinoline (130-16-5)

Guidance literature:

With trichloroisocyanuric acid; In acetonitrile; at 20 ℃; regioselective reaction;

DOI:10.1039/c7sc04107a

upstream raw materials:

8-quinolinol

broxyquinoline

5,7,7-trichloro-7H-quinoline-8-one

2,4-dichloro-6-nitrophenol

Downstream raw materials:

undec-10-enoic acid-(5,7-dichloro-[8]quinolyl ester)

benzoic acid-(5,7-dichloro-[8]quinolyl ester)

β-D-glucose

5-Chloro-8-hydroxyquinoline

Refernces

• 1、 Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake. "A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines". . p. 1782 - 1788. Retrieved 2018/02/23.
• 2、 Oliveri, Valentina,Viale, Maurizio,Caron, Giulia,Aiello, Cinzia,Gangemi, Rosaria,Vecchio, Graziella. "Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy". supporting information. p. 2023 - 2034. Retrieved 2013/03/14.