5-Chloro-8-hydroxyquinoline
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5-Chloro-8-hydroxyquinoline
structure -
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CAS No:
130-16-5
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Formula:
C9H6ClNO
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Chemical Name:
5-Chloro-8-hydroxyquinoline
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Synonyms:
8-Quinolinol,5-chloro-;5-Chloro-8-quinolinol;5-Chloro-8-hydroxyquinoline;Dermofungin;Dermofongin;5-Chloro-8-oxyquinoline;Cloxyquin;5-Chlorooxine;8-Hydroxy-5-chloroquinoline;Cloxiquine;NSC 35083;NSC 53182;NSC 74943;5-Chloro-quinoline-8-ol
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Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs
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CAS No:
Description
light green to grey powder
Cloxiquine is a member of quinolines and an organochlorine compound.|Cloxyquin is a monohalogenated 8-hydroxyquinoline with activity against bacteria, fungi, and protozoa. Cloxyquin is reported to have activity against Mycobacterium tuberculosis, including strains that show resistance to common first-line antibacterial agents.
5-Chloro-8-hydroxyquinoline Basic Attributes
179.6
179.60
5289
204-978-1
BPF36H1G6S
756701|53182|35083
DTXSID4045973
C61689
29334990
Characteristics
33.1
2.9
Light green to gray Powder
1.2364 (rough estimate)
130 °C
348.7±22.0 °C(Predicted)
164.7±22.3 °C
1.5330 (estimate)
0.019g/l (experimental)
Store below +30°C.
2.46E-05mmHg at 25°C
129.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
NONH for all modes of transport
3
36/37/38
26-36-24/25
VC4590000
Xi
Stable at room temperature in closed containers under normal storage and handling conditions.
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (99.61%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 260 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Chloro-8-hydroxyquinoline Use and Manufacturing
General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 °C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7−8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15percent ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.
antibacterial, antifungal
8-Quinolinol, 5-chloro-: ACTIVE
Computed Properties
Molecular Weight:179.60
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:179.0137915
Monoisotopic Mass:179.0137915
Topological Polar Surface Area:33.1
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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