5-(Chloromethyl)-8-quinolinol hydrochloride

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5-(Chloromethyl)-8-quinolinol hydrochloride manufacturers

5-(Chloromethyl)-8-quinolinol hydrochloride Basic information
Product Name:5-(Chloromethyl)-8-quinolinol hydrochloride
Synonyms:5-(Chloromethyl)-8-hydroxyquinoline hydrochloride;8-quinolinol, 5-(chloromethyl)-;5-(Chloromethyl)-8-quinolinol;8-Quinolinol, 5-(chloromethyl)-, hydrochloride;Aids125750;Aids-125750;Nsc83066;5-(CHLOROMETHYL)QUINOLIN-8-OL HYDROCHLORIDE
CAS:4053-45-6
MF:C10H9Cl2NO
MW:230.09
EINECS:
Product Categories:
Mol File:4053-45-6.mol
5-(Chloromethyl)-8-quinolinol hydrochloride Structure
5-(Chloromethyl)-8-quinolinol hydrochloride Chemical Properties
Melting point 280 °C (decomp)
storage temp. 2-8°C
EPA Substance Registry System8-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1) (4053-45-6)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 22
TSCA TSCA listed
HazardClass IRRITANT
HS Code 2933499090
MSDS Information
5-(Chloromethyl)-8-quinolinol hydrochloride Usage And Synthesis
Synthesis
8-Hydroxyquinoline

148-24-3

Formaldehyde

50-00-0

5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE

4053-45-6

14.6 g (0.1 mol) of 8-hydroxyquinoline, 16 mL of 32% aqueous hydrochloric acid and 16 mL (0.1 mol) of 37% aqueous formaldehyde were mixed at 0°C and passed through hydrogen chloride gas to react for 6 hours. After completion of the reaction, the mixture was allowed to stand at room temperature for 2 hours without stirring. The yellow solid produced by the reaction was collected by filtration, washed with 90% ethanol and dried under vacuum to afford 5-(chloromethyl)-8-quinolinol hydrochloride (19.0 g, 98% yield). The structure of the product was confirmed by 1H NMR (250 MHz, CDCl3): δ 5.32 (s, 2H), 7.53 (m, 1H), 7.85 (m, 2H), 8.12 (m, 1H), 9.12 (m, 1H), 9.28 (m, 1H).

References[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10455 - 10463
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 3, p. 773 - 783
[3] Patent: WO2012/20389, 2012, A1. Location in patent: Page/Page column 22
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8616 - 8637
[5] Journal of Molecular Liquids, 2016, vol. 219, p. 396 - 404
5-(Chloromethyl)-8-quinolinol hydrochloride Preparation Products And Raw materials
Raw materials8-Hydroxyquinoline-->Formaldehyde-->Hydrochloric acid
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