5-Chloro-8-hydroxyquinoline

Base Information

• Chemical Name: 5-Chloro-8-hydroxyquinoline
• CAS No.: 130-16-5
• Molecular Formula: C9H6ClNO
• Molecular Weight: 179.606
• Hs Code.: 2933.40
• European Community (EC) Number: 204-978-1
• NSC Number: 756701,53182,35083
• UNII: BPF36H1G6S
• DSSTox Substance ID: DTXSID4045973
• Nikkaji Number: J2.942D
• Wikidata: Q27274791
• NCI Thesaurus Code: C61689
• Pharos Ligand ID: KHLXCF9HN7RW
• Metabolomics Workbench ID: 144331
• ChEMBL ID: CHEMBL225164
• Mol file: 130-16-5.mol

Synonyms:5-chloro-8-hydroxyquinoline;5-chloro-8-hydroxyquinoline hydrochloride

Chemical Property of 5-Chloro-8-hydroxyquinoline

Chemical Property:

• Appearance/Colour: light green to grey powder
• Vapor Pressure: 2.46E-05mmHg at 25°C
• Melting Point: 122-124 °C(lit.)
• Refractive Index: 1.696
• Boiling Point: 348.7 °C at 760 mmHg
• PKA: 3.77±0.10(Predicted)
• Flash Point: 164.7 °C
• PSA: 33.12000
• Density: 1.412 g/cm³
• LogP: 2.59380
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 0.019g/l (experimental)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 179.0137915
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

Dermofungin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=C2N=C1)O)Cl
• Uses: antibacterial, antifungal Dermofungin, is an impurity of Cioquinol, which is an antifungal and antiprotozoal drug.

Technology Process of 5-Chloro-8-hydroxyquinoline

There total 20 articles about 5-Chloro-8-hydroxyquinoline 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: 100.0%

5-chloro-7-iodoquinolin-8-ol (130-26-7,22112-03-4) → 5-Chloro-8-hydroxyquinoline (130-16-5)

Guidance literature:

With piperidine; palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 50 ℃; for 24h; under 750.075 Torr; Autoclave;

DOI:10.1080/00397910802542028

Reference yield: 93.0%

5-bromo-8-hydroxyquinoline (1198-14-7) → 5-Chloro-8-hydroxyquinoline (130-16-5)

Guidance literature:

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

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

Reference yield: 92.0%

5-chloro-7-iodoquinolin-8-yl ethanoate (27037-46-3) → 5-Chloro-8-hydroxyquinoline (130-16-5)

Guidance literature:

With pyridine; water; Heating;

DOI:10.1021/jo051191x

upstream raw materials:

8-quinolinol

8-Hydroxyquinoline hydrochloride

p-chloro-o-nitrophenol

glycerol

Downstream raw materials:

5-(N-phenylanilino)quinolin-8-ol

Refernces

• 1、 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". . p. 2023 - 2034. Retrieved 2013.
• 2、 Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma. "Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes". . p. 1121 - 1126. Retrieved 2018/08/17.
• 3、 Ramann, Ginelle A.,Cowen, Bryan J.. "Quinoline synthesis by improved Skraup-Doebner-Von Miller reactions utilizing acrolein diethyl acetal". supporting information. p. 6436 - 6439. Retrieved 2015/11/16.