4-Methoxy-pyridine-2-carboxylic acid metyl ester

4-Methoxy-pyridine-2-carboxylic acid metyl ester - Names and Identifiers

Name	Methyl 4-methoxypyridine-2-carboxylate
Synonyms	METHYL 4-METHOXYPICOLINATE methyl 4-methoxypyridin-2-carboxyate Methyl 4-methoxypyridine-2-carboxylate METHYL 4-METHOXY-2-PYRIDINECARBOXYLATE METHYL 4-METHOXYPYRIDINE-2-CARBOXYLATE 4-Methoxy-pyridine-2-carboxylic acid metyl ester 4-Methoxypyridine-2-carboxylic acid methyl ester 4-methoxy-pyridine-2-carboxylic acid methyl ester 4-METHOXY-2-PYRIDINE CARBOXYLIC ACID METHYL ESTER 4-METHOXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
CAS	29681-43-4
EINECS	685-565-7
InChI	InChI=1/C8H9NO3/c1-11-6-3-4-9-7(5-6)8(10)12-2/h3-5H,1-2H3

4-Methoxy-pyridine-2-carboxylic acid metyl ester - Physico-chemical Properties

Molecular Formula	C8H9NO3
Molar Mass	167.16
Density	1.156±0.06 g/cm3(Predicted)
Melting Point	47-50
Boling Point	280.4±20.0 °C(Predicted)
Flash Point	123.4°C
Solubility	DMSO (Slightly), Methanol (Very Slightly)
Vapor Presure	0.0038mmHg at 25°C
Appearance	Solid
Color	Pale Yellow
pKa	2.44±0.10(Predicted)
Storage Condition	Inert atmosphere,Room Temperature
Refractive Index	1.503
MDL	MFCD00956223

4-Methoxy-pyridine-2-carboxylic acid metyl ester - Risk and Safety

Hazard Symbols	Xi - Irritant
WGK Germany	3
Hazard Class	IRRITANT

4-Methoxy-pyridine-2-carboxylic acid metyl ester - Reference Information

application

methyl 4-methoxypicolinic acid is an organic intermediate that can be made of 2-picolinic acid As a raw material, 4-chloro-2-picolinic acid is first chlorinated, and then reacted with methanol to prepare methyl 4-methoxypicolinic acid.

Preparation

2-picolinic acid (9.92g,80.7mmol) and sodium bromide (0.90g,8.7mmol) were added to thionyl chloride (70mL), and the mixture was heated and refluxed for 16 hours.
The reaction was vacuum concentrated and cooled to 0°C. MeOH(30mL) was carefully added and the reaction was heated and refluxed for 36 h. Vacuum removed the solvent, dissolved the residue in CH2Cl2(100mL), added sodium carbonate (12.8g,121mmol), and stirred the mixture for 3 hours. H2O(100mL) was added and the reaction was extracted with CH2Cl2(5 × 50mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuum. The crude residue was purified by rapid column chromatography (SiO2, eluted with Et2O, then eluted with a 5:95 MeOH-CH2Cl2) and recrystallized (hexane) to give the white acicular product methyl 4-methoxypicolinate (9.03g,67%).

Last Update：2024-04-09 20:52:54