Methyl 6-bromonicotinate Chemical Properties

Melting point:

119-121

Boiling point:

107-110 °C(Press: 4 Torr)

Density 

1.579±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

-1.25±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

InChI

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

InChIKey

NFLROFLPSNZIAH-UHFFFAOYSA-N

SMILES

C1=NC(Br)=CC=C1C(OC)=O

CAS DataBase Reference

26218-78-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2933399990

Methyl 6-bromonicotinate Usage And Synthesis

Uses

A potential hypolipidemic agent; a nicotinic acid analog. Heterocyclic compounds affecting free fatty acid mobilization in vivo.

Synthesis

A 100 mL round bottom flask was charged with 6-bromonicotinic acid (540 mg, 2.7 mmol), methylene chloride (20 mL) and N,N-dimethylformamide (1 drop). Oxalyl chloride (1 mL) was then added slowly and vigorous gas escape was observed. The reaction mixture was stirred at room temperature for 1 h, after which the solvent was removed under reduced pressure by rotary evaporator. The residue was treated with methanol (MeOH) and the solvent was again removed under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate (NaHCO3) solution. The organic layer was dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give 369 mg of methyl 6-bromonicotinate in 55% yield. The product was characterized by 1H NMR (500 MHz): δ 9.00 (dd, J = 2.0, 0.5 Hz, 1H), 8.25 (dd, J = 8.5, 2.5 Hz, 1H), 7.42 (dd, J = 8.5, 0.5 Hz, 1H), 3.96 (s, 3H).

References

[1] Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13445 - 13454
[2] Heterocycles, 1994, vol. 38, # 7, p. 1551 - 1572
[3] Patent: WO2008/21388, 2008, A1. Location in patent: Page/Page column 191-192
[4] Patent: WO2018/126072, 2018, A1. Location in patent: Paragraph 0255; 0256
[5] Patent: US2014/18368, 2014, A1. Location in patent: Paragraph 0162; 0174

Methyl 6-bromonicotinate(26218-78-0)Related Product Information

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