Identification | Back Directory | [Name]
2-Chloro-6-hydroxyquinoline | [CAS]
577967-89-6 | [Synonyms]
2-chloroquinolin-6-ol 2-chloro-6-Quinolinol 6-Quinolinol, 2-chloro- 2-Chloro-6-hydroxyquinoline | [Molecular Formula]
C9H6ClNO | [MDL Number]
MFCD12405093 | [MOL File]
577967-89-6.mol | [Molecular Weight]
179.6 |
Chemical Properties | Back Directory | [Melting point ]
192℃ | [Boiling point ]
342.1±22.0 °C(Predicted) | [density ]
1.412 | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Acetonitrile (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
8.62±0.40(Predicted) | [color ]
Pale Beige | [InChI]
InChI=1S/C9H6ClNO/c10-9-4-1-6-5-7(12)2-3-8(6)11-9/h1-5,12H | [InChIKey]
XANCOYIVTNZKOE-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC(O)=CC=2)C=CC=1Cl |
Hazard Information | Back Directory | [Uses]
2-Chloroquinolin-6-ol can be used for hair dye compositions. | [Definition]
ChEBI: 2-chloroquinolin-6-ol is a monohydroxyquinoline that is 6-hydroxyquinoline in which the hydrogen at position 2 is replaced by a chlorine. It is an organochlorine compound and a monohydroxyquinoline. | [Synthesis]
The general procedure for the synthesis of 2-chloro-6-hydroxyquinoline from 2-chloro-6-methoxyquinoline is as follows: General method: aryl methyl ether (1.0 eq.) was dissolved in dichloromethane (DCM, 10 mL) and cooled to 0 °C. Boron tribromide (BBr3, 5.0 eq.) was added slowly under stirring. The reaction mixture was stirred at 0 °C and then gradually warmed to room temperature and continued stirring at room temperature for 15 hours. Upon completion of the reaction, the reaction was quenched with sodium bicarbonate (NaHCO3) solution (50 mL) followed by extraction with DCM (4 x 10 mL). The organic layers were combined, washed with water (3 × 10 mL), dried over anhydrous sodium sulfate (Na2SO4), and finally concentrated under vacuum to obtain the target phenolic compounds. 2-Chloro-6-hydroxyquinoline (DHK-6-71) was prepared from 2 g scale of 2-chloro-6-methoxyquinoline using the above general method G. The product was a yellow solid in 93% (1.72 g) yield. | [References]
[1] Patent: CN102985411, 2016, B. Location in patent: Paragraph 0906-0908 [2] Patent: WO2012/48181, 2012, A1. Location in patent: Page/Page column 74 [3] Patent: WO2012/83165, 2012, A1. Location in patent: Page/Page column 91 [4] ACS Chemical Neuroscience, 2016, vol. 7, # 7, p. 897 - 911 [5] Journal of the American Chemical Society, 1951, vol. 73, p. 4837 |
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