| Identification | More | [Name]
3-Bromo-2-hydroxypyridine | [CAS]
13466-43-8 | [Synonyms]
2-HYDROXY-3-BROMOPYRIDINE
3-BROMO-2(1H)-PYRIDINONE
3-BROMO-2-HYDROXYPYRIDINE
3-BROMO-2-PYRIDINOL
3-BROMO-2-PYRIDONE
3-BROMO-PYRIDIN-2-OL
IFLAB-BB F1371-0174
3-Bromo-2-Hydroxypyridine99%
3-Bromo-2(1H)-pyridone | [EINECS(EC#)]
626-942-8 | [Molecular Formula]
C5H4BrNO | [MDL Number]
MFCD03411569 | [Molecular Weight]
174 | [MOL File]
13466-43-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow powder | [Melting point ]
179-183 °C | [Boiling point ]
336.6±42.0 °C(Predicted) | [density ]
1.776±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
Crystalline Powder | [pka]
10.53±0.10(Predicted) | [color ]
White to off-white | [Water Solubility ]
Slightly soluble in water. | [BRN ]
109846 | [InChI]
InChI=1S/C5H4BrNO/c6-4-2-1-3-7-5(4)8/h1-3H,(H,7,8) | [InChIKey]
YDUGVOUXNSWQSW-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=CC=C1Br | [CAS DataBase Reference]
13466-43-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HS Code ]
29337900 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow powder | [Uses]
3-Bromo-2-hydroxypyridine is sued as an active ingredient pharmaceuticals, in medicine. | [Uses]
3-Bromo-2-hydroxypyridine is used in the synthesis of pyrazolopyridines as γ-secratase modulators. | [Synthesis]
The general procedure for the synthesis of 3-bromo-2-hydroxypyridine from 2-amino-3-bromopyridine was as follows: sodium nitrite (24.2 g, 0.35 mol, 4.84 eq.) was dissolved in water (175 mL) at 0 °C and slowly added dropwise to a solution containing 2-amino-3-bromopyridine (12.5 g, 72.4 mmol) and sulfuric acid (35 mL, 0.66 mol , 9.10 eq.) in a solution of water (175 mL). The reaction mixture was stirred at 0 °C for 1 hour. Subsequently, the reaction mixture was neutralized with sodium hydroxide solution to pH=7. The neutralized solution was extracted with chloroform (3 x 200 mL), the organic phases were combined and washed with brine (200 mL), dried over magnesium sulfate, filtered and concentrated in vacuum to afford the milky white solid product 3-bromo-2-hydroxypyridine (11.3 g, 90% yield). The product was characterized as follows: melting point 183 °C; IR (pure) νmax 3339, 3105, 2991, 2942, 1776, 1650, 1610, 1464 cm-1; 1H NMR (500 MHz, CDCl3) δ 7.87 (dd, J = 7.3, 1.9 Hz, 1H), 7.49 (dd, J = 6.4, 1.9 Hz, 1H), 6.24 (dd, J = 7.3, 6.4 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ 161.9, 143.9, 134.4, 115.7, 107.7 ppm; HRMS (ESI) m/z [M + Na]+ Calculated value: 195.9369, measured value: 195.9373 (deviation +2.07 ppm). | [References]
[1] Organic Letters, 2016, vol. 18, # 13, p. 3106 - 3109
[2] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588 |
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