Name | 2-Hydroxynicotinic acid |
Synonyms | 2-HYDROXYNICOTINIC ACID 2-Hydroxynicotinic acid 2-Hydroxy-3-picolinic acid 1,2-dihydro-2-oxonicotinic acid 2-HYDROXY-3-PYRIDINECARBOXYLIC ACID 2-Hydroxypyridine-3-carboxylic acid 2-HYDROXYPYRIDINE-3-CARBOXYLIC ACID 2-Hydroxy-3-Pyridine Carboxylic acid 2-oxo-1,2-dihydropyridine-3-carboxylate 2-oxo-1,2-dihydropyridine-3-carboxylic acid 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo- |
CAS | 609-71-2 |
EINECS | 210-198-2 |
InChI | InChI=1/C6H5NO3/c8-5-4(6(9)10)2-1-3-7-5/h1-3H,(H,7,8)(H,9,10)/p-1 |
InChIKey | UEYQJQVBUVAELZ-UHFFFAOYSA-N |
Molecular Formula | C6H5NO3 |
Molar Mass | 139.11 |
Density | 1.4429 (rough estimate) |
Melting Point | 258-261°C(lit.) |
Boling Point | 255.04°C (rough estimate) |
Flash Point | 217.5°C |
Solubility | formic acid: soluble50 mg/mL, clear, colorless to yellow |
Vapor Presure | 8.03E-09mmHg at 25°C |
Appearance | White to bright yellow powder |
Color | White to light yellow |
BRN | 119028 |
pKa | 2.40±0.20(Predicted) |
Storage Condition | Inert atmosphere,Room Temperature |
Refractive Index | 1.5423 (estimate) |
MDL | MFCD00010100 |
Use | 2-Hydroxynicotinic Acid may be used in chemical synthesis |
Hazard Symbols | Xi - Irritant![]() |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
WGK Germany | 3 |
HS Code | 29333990 |
Hazard Class | IRRITANT |
Introduction | 2-hydroxynicotinic acid is an organic intermediate, it is reported that 2-hydroxynicotinic acid can be prepared from 3-bromo-2-hydroxypyridine or 3-cyano-2-pyridone in one step |
Use | 2-hydroxynicotinic acid is an analog of nicotinic acid, as a growth factor for the growth of Erwinia (Flowers of pears and apples). |
preparation | 3-bromo-2-hydroxypyridine (0.76g, to a solution of 4.4 mmol,1.0 equiv) in anhydrous THF(20 ml) was added a 2 M solution of i-PrMgCl THF(2.2 ml,1.0 equiv). The clear solution was stirred at this temperature for an additional 5 minutes, and a 2.5 M solution of N-butyllithium in hexane (3.5 ml,2.0 eq) was added dropwise over 5 minutes while maintaining the temperature below -20 °c. The resulting mixture was stirred at this temperature for 0.5 H and dry CO2(0.20g,1.0 eq) was added to the -20 °c system. The resulting mixture was heated to -20 °c over 0.5 H and quenched with water (6ml). After the mixture was stirred for 10 minutes at below -20 °c, the phases were separated and the aqueous phase was extracted once more with ethyl acetate. The resulting suspension was allowed to reach room temperature and filled through a 0.5 x 1 pad of silica gel, eluting with 10ml of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 10:1) to give the product 2-hydroxynicotinic acid as an off-white solid, 0.48g (yield: 79%),mp:255-257 degrees Celsius. |
Application | 2-hydroxynicotinic acid is a white to pale yellow powder that is useful as a pharmaceutical intermediate. |