| Identification | More | [Name]
2-Chloro-4-hydroxypyridine | [CAS]
17368-12-6 | [Synonyms]
2-CHLORO-4-HYDROXYPYRIDINE
2-CHLORO-4-PYRIDINOL
2-CHLOROPYRIDIN-4-OL
4-Pyridinol,2-chloro-(7CI,8CI,9CI)
2-Chloro-4-hydroxypyridine HCl Salt
2-CHLORO-4-HYDROXYPYRIDINE 99%
2-Chloro-4-hydroxypyridine hydrochloride | [EINECS(EC#)]
241-399-3 | [Molecular Formula]
C5H4ClNO | [MDL Number]
MFCD01646108 | [Molecular Weight]
129.54 | [MOL File]
17368-12-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystal | [Melting point ]
169-172°C | [Boiling point ]
401.8±25.0 °C(Predicted) | [density ]
1.392±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
7.94±0.10(Predicted) | [color ]
White to Light yellow to Light orange | [InChI]
InChI=1S/C5H4ClNO/c6-5-3-4(8)1-2-7-5/h1-3H,(H,7,8) | [InChIKey]
VBEHFOMFHUQAOW-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC(O)=C1 | [CAS DataBase Reference]
17368-12-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Chemical Properties]
White crystal | [Uses]
2-Chloro-4-hydroxypyridine is a chemical that is used as a building block for various organic synthesis reactions. | [Preparation]
2-Chloro-4-hydroxypyridine can be produced by the reaction of chloroform and pyridine, which results in the formation of 2-chloro-4-hydroxypyridine.
| [Reactions]
2-Chloro-4-hydroxypyridine has been shown to react with copper metal under dehydrogenative conditions to form monochloropyridine. It also reacts with tribromide to form tribromopyridine and with graphene oxide to form hydroxypyridinium bromide. Lastly, it reacts with an organic solvent such as acet.
| [Synthesis]
The general procedure for the synthesis of 2-chloro-4-hydroxypyridine from 2-chloro-4-aminopyridine is as follows: in a round-bottomed flask, 2-chloro-4-aminopyridine (3.0 g, 23.3 mmol) was dissolved in 40% sulfuric acid solution (50 g). The solution was stirred at 0 °C and sodium nitrite (1.93 g, 28.0 mmol) was added slowly. After addition, the reaction mixture was stirred continuously at room temperature for 24 hours. Upon completion of the reaction, the reaction solution was neutralized by dropwise addition of aqueous sodium hydroxide and aqueous sodium bicarbonate. Subsequently, the organic phase was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, distilled to remove the solvent and dried under reduced pressure to give 2-chloro-4-hydroxypyridine (light brown solid, 2.78 g, 92% yield). The product was characterized by 1H-NMR (270 MHz, DMSO-d6): δ 11.20 (s, 1H, -OH), 8.09 (d, 1H, J = 5.4 Hz, ArH), 6.81 (s, 1H, ArH), 6.77 (d, 1H, J = 2.2 Hz, ArH). | [References]
[1] Patent: WO2009/11447, 2009, A2. Location in patent: Page/Page column 37-38 |
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