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| | 2-Hydroxynicotinic acid Basic information | | Synthesis |
| | 2-Hydroxynicotinic acid Chemical Properties |
| Melting point | 258-261 °C(lit.) | | Boiling point | 255.04°C (rough estimate) | | density | 1.4429 (rough estimate) | | refractive index | 1.5423 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | 0.1 M NaOH: 0.1 g/mL, clear | | pka | 2.40±0.20(Predicted) | | form | Powder | | color | White to light yellow | | BRN | 119028 | | InChI | InChI=1S/C6H5NO3/c8-5-4(6(9)10)2-1-3-7-5/h1-3H,(H,7,8)(H,9,10) | | InChIKey | UEYQJQVBUVAELZ-UHFFFAOYSA-N | | SMILES | C1(=O)NC=CC=C1C(O)=O | | CAS DataBase Reference | 609-71-2(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29333990 | | Storage Class | 11 - Combustible Solids |
| | 2-Hydroxynicotinic acid Usage And Synthesis |
| Synthesis | 
At 0°C, 2 M i-PrMgCl THF (2.2 ml, 1.0 equivalent) solution was added over 5 minutes to an anhydrous THF (20 ml) solution of 3-bromo-2-hydroxypyridine (0.76 g, 4.4 mmol, 1.0 equivalent). The clear solution was stirred at this temperature for another 5 minutes, and a 2.5 M hexane solution of n-butyllithium (3.5 ml, 2.0 equivalent) was added dropwise over 5 minutes while maintaining the temperature below -20°C. The resulting mixture was stirred at this temperature for 0.5 hours, and dried CO2 (0.20 g, 1.0 equivalent) was added to the -20°C system. The resulting mixture was heated to -20°C over 0.5 hours and quenched with water (6 ml). After stirring the mixture below -20°C for 10 minutes, the phases were separated, and the aqueous phase was extracted once more with ethyl acetate. The resulting suspension was brought to room temperature and passed through a 0.5 × 1 cm silica gel sieve, eluted with 10 ml of ethyl acetate. The filtrate was concentrated, and the residue was purified by rapid silica gel chromatography (eluent: petroleum ether/ethyl acetate = 10:1) to give the product 2-hydroxynicotinic acid, a grayish-white solid, 0.48 g (yield: 79%), mp: 255–257°C. | | Chemical Properties | White to light yellow powder | | Uses | 2-Hydroxynicotinic acid is used in chemical synthesis. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields. | | Definition | ChEBI: 2-Hydroxynicotinic acid is a member of pyridines and an aromatic carboxylic acid. It is a derivative of nicotinic acid, was found to exist in four polymorphs. It is used as a growth factor in Erwinia amylovora growth (pear and apple blossoms). |
| | 2-Hydroxynicotinic acid Preparation Products And Raw materials |
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