methyl 3-bromopicolinate Chemical Properties

Boiling point:

267.4±20.0 °C(Predicted)

Density 

1.579±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

-0.91±0.10(Predicted)

form 

solid

color 

Pale yellow

InChI

InChI=1S/C7H6BrNO2/c1-11-7(10)6-5(8)3-2-4-9-6/h2-4H,1H3

InChIKey

GSTYLUGZSCVBTJ-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=CC=C1Br

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

HazardClass 

IRRITANT

HS Code 

2933399990

methyl 3-bromopicolinate Usage And Synthesis

Synthesis

a) To a methanolic solution of 3-bromo-2-pyridinecarboxylic acid (1 g, 4.9 mmol), a few drops of concentrated sulfuric acid were slowly added as a catalyst at room temperature. The reaction mixture was stirred at room temperature for 12 hours to ensure complete reaction. Upon completion of the reaction, methanol was removed by rotary evaporation to give the crude product. The crude product was purified by a CombiFlash fast chromatography system on a silica gel column with the eluent being a hexane solution of 20-50% ethyl acetate, resulting in methyl 3-bromopyridinecarboxylate (450 mg, 41% yield). Subsequently, compound 17 (82% yield) was synthesized in a series of reaction steps according to the method described in Example 1 using methyl 3-bromopyridinecarboxylate as starting material, and compound 4 was finally prepared.

References

[1] Patent: US2011/136833, 2011, A1. Location in patent: Page/Page column 27
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 635 - 654
[3] Patent: US3963733, 1976, A

methyl 3-bromopicolinate(53636-56-9)Related Product Information

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• 3-BROMOPYRIDINE-2-CARBOXYLIC ACID
• 3-Bromo-5-chloropyridine
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