4-IODO-3-HYDROXYPYRIDINE
4-IODO-PYRIDIN-3-OL
CAS: 188057-20-7
Molecular Formula: C5H4INO
4-IODO-3-HYDROXYPYRIDINE - Names and Identifiers
| Name | 4-IODO-PYRIDIN-3-OL |
| Synonyms | AKOS A0602-0922 2-Iodo-3-pyridinol 4-IODO-PYRIDIN-3-OL 3-Pyridinol, 4-iodo- 4-IODO-3-HYDROXYPYRIDINE 3-Hydroxy-4-iodopyridine 2-Iodo-3-hydroxypyridine |
| CAS | 188057-20-7 |
4-IODO-3-HYDROXYPYRIDINE - Physico-chemical Properties
| Molecular Formula | C5H4INO |
| Molar Mass | 221 |
| Melting Point | 196-200℃ |
| Boling Point | 296.603℃ at 760 mmHg |
| Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
4-IODO-3-HYDROXYPYRIDINE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. |
4-IODO-3-HYDROXYPYRIDINE - Reference Information
| overview | 4-iodo-3-hydroxypyridine is an organic intermediate, commonly used in the synthesis of various pharmaceutical and chemical products. There are reports in the literature that 4-iodo-3-hydroxypyridine can be prepared from 2-chloro-4-iodopyridine in one step or from 3-hydroxypyridine in three steps. |
| application | 4-iodo-3-hydroxypyridine is an organic intermediate and pharmaceutical intermediate, commonly used in the synthesis of various pharmaceutical and chemical products and laboratory research and development process. |
| Preparation | Potassium tert-butoxide (3.71g,33 mmol,1.1 equivalent) was added to the DMF/THF mixture (8:3,21 mL) of 3-hydroxypyridine (2.85g,30 mmol) under nitrogen atmosphere at -15°C. After 20 minutes, methoxymethyl chloride (MOMC1,2.5mL,31.5mmol,1.05 equivalent) was added, and after another hour, saline (20mL) and water (20mL) were added sequentially. The mixture was extracted with ethyl acetate (3 × 30mL), the combined organic phase was washed with brine (2 × 40mL), dried with magnesium sulfate, and concentrated in vacuum. The residue was distilled under vacuum to provide 3-methoxymethoxypyridine (2.76g,19.8mmol,66%). In a nitrogen atmosphere, tert-butyl lithium (1.35 M pentane solution, 8.2 mL,11 mmol,1.1 equivalent) was added to a solution of 3-methoxymethoxypyridine (1.39g,10 mmol) in anhydrous Et2O(50 mL) at -78°C. After 20 minutes, add iodine (3.04g,12mmol,1.2 equivalent) Et2O(30mL) solution, and keep the reaction mixture at -78°C for 1h. Add water (40mL) and separate the phases. The aqueous phase was extracted with Et2O(2 × 25mL), the combined organic phase was washed with brine (40mL), dried with magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography (50% a heptane solution of ethyl acetate) to give 4-iodo-3-methoxymethoxypyridine (2.05g,7.73mmol,77%). 4-iodo-3-methoxymethoxypyridine (1.55g,5.84mmol) and PTSA(100mg) were partitioned between water (10mL) and Et2O(5mL). The resulting mixture was refluxed and heated for 16 hours; the ether was then evaporated and an aliquent of water (10mL) was added. After refluxing for another 8 hours, the mixture was cooled to room temperature and collected by filtration to obtain 4-iodo-3-hydroxypyridine (807mg,3.65mmol,62%). |
Last Update：2024-04-09 02:00:02
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