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ChemicalBook--->CAS DataBase List--->29681-43-4

29681-43-4

29681-43-4 Structure

29681-43-4 Structure
IdentificationMore
[Name]

4-METHOXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
[CAS]

29681-43-4
[Synonyms]

4-METHOXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
METHYL 4-METHOXY-2-PYRIDINECARBOXYLATE
METHYL 4-METHOXYPICOLINATE
METHYL 4-METHOXYPYRIDINE-2-CARBOXYLATE
Methyl 4-methoxypyridine-2-carboxylate 97%
4-METHOXY-2-PYRIDINE CARBOXYLIC ACID METHYL ESTER
methyl 4-methoxypyridin-2-carboxyate
4-Methoxy-pyridine-2-carboxylic acid metyl ester
[EINECS(EC#)]

685-565-7
[Molecular Formula]

C8H9NO3
[MDL Number]

MFCD00956223
[Molecular Weight]

167.16
[MOL File]

29681-43-4.mol
Chemical PropertiesBack Directory
[Melting point ]

47-50
[Boiling point ]

280.4±20.0 °C(Predicted)
[density ]

1.156±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Very Slightly)
[form ]

Solid
[pka]

2.44±0.10(Predicted)
[color ]

Pale Yellow
[InChI]

InChI=1S/C8H9NO3/c1-11-6-3-4-9-7(5-6)8(10)12-2/h3-5H,1-2H3
[InChIKey]

OJDKENGKKYVJLY-UHFFFAOYSA-N
[SMILES]

C1(C(OC)=O)=NC=CC(OC)=C1
[CAS DataBase Reference]

29681-43-4(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

Methyl 4-methoxypicolinate is a useful intermediate for the synthesis of substituted terpyridine ligands for use in protein purification.
[Synthesis]

2-Picolinic acid

98-98-6

Methanol

67-56-1

Sodium Methoxide

124-41-4

4-METHOXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER

29681-43-4

GENERAL STEPS: 2-Pyridinecarboxylic acid (5.0 g, 40.6 mmol) was dissolved in SOCl2 (15 mL) cooled to 0 °C, H2O (950 μL) was added slowly, followed by refluxing the reaction mixture for 1 hour. After the reaction mixture was cooled to room temperature, SOCl2 (15 mL) was added additionally and the reaction was continued to reflux for 2 days. After cooling to room temperature again, a third batch of SOCl2 (15 mL) was added and the mixture was continued to reflux for 2 days. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the resulting residue was dissolved in MeOH (30 mL) and refluxed overnight. Subsequently, a solution of NaOMe (4.4 g, 81.2 mmol) in MeOH (50 mL) was added to the reaction system and the reaction was continued at reflux for 2 days. At the end of the reaction, the solvent was removed by distillation under reduced pressure and the residue was dissolved in water and extracted with CHCl3. The organic phases were combined, dried with MgSO4 and concentrated under reduced pressure. The crude product was purified by SiO2 fast column chromatography with the eluent ratio of hexane:AcOEt = 1:1→1:4→1:10 to obtain the target product. Finally, the resulting solid was washed with hexane-Et2O (1:1) to afford methyl 4-methoxypyridine-2-carboxylate (1.8 g, 26% yield) as a light yellow solid.

[References]

[1] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
Spectrum DetailBack Directory
[Spectrum Detail]

4-METHOXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER(29681-43-4)1HNMR
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