5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Melting point:

101-103°C

Boiling point:

290.9±20.0 °C(Predicted)

Density 

1.579±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-0.67±0.10(Predicted)

color 

White to Almost white

Water Solubility 

Soluble in water.

InChI

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

InChIKey

JEURNBCYNWNADN-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=C(Br)C=C1

CAS DataBase Reference

29682-15-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-37

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 5-bromopyridine-2-carboxylate is used as an organic chemical synthesis intermediate.

Synthesis

Example 89 - Preparation of Intermediate 25: The synthesis of Intermediate 25 followed the following general procedure. To a solution of 5-bromopyridine-2-carboxylic acid (50.0 g, 0.247 mol, 1.0 eq.) in anhydrous methanol (400 mL) cooled to 0 °C was added thionyl chloride (107.0 mL, 2.47 mol, 10.0 eq.) dropwise. The reaction mixture was slowly warmed to room temperature and subsequently heated at 50 °C for 12 hours. The reaction process was monitored by thin layer chromatography (TLC) and liquid chromatography-mass spectrometry (LC-MS). After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a white solid residue. The residue was slowly quenched with saturated sodium bicarbonate solution and the white solid was collected by filtration to afford the target product methyl 5-bromopyridine-2-carboxylate (43.0 g, 80% yield). The product was characterized by mass spectrometry (m/z 216.14) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, DMSO): δ 8.86 (d, J=1.9 Hz, 1H), 8.28 (dd, J=8.4,2.4 Hz, 1H), 8.00 (d, J=8.4 Hz, 1H), 3.89 (s, 3H) ppm.

References

[1] Patent: WO2018/126072, 2018, A1. Location in patent: Paragraph 0246; 0247
[2] Patent: WO2012/76898, 2012, A1. Location in patent: Page/Page column 64-65
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 22, p. 4780 - 4784
[4] Patent: WO2016/44662, 2016, A1. Location in patent: Paragraph 00379-00380
[5] Patent: CN103360407, 2016, B. Location in patent: Paragraph 0135-0137

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