Methyl 5-bromonicotinate Chemical Properties

Melting point:

96-100 °C

Boiling point:

241.7±20.0 °C(Predicted)

Density 

1.579±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

solid

pka

0.84±0.20(Predicted)

color 

White

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

AAJZXPWBILCHAW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

29681-44-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-39-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl 5-bromonicotinate Usage And Synthesis

Chemical Properties

white powder

Uses

A substrate used in a microwave-assisted, palladium-catalyzed arylation of acetone as its TMS enol ether.

Application

Methyl 5-bromonicotinate could be used to synthesize Pyridine alkaloids from Rubiaceae with various organometallic reagents by palladium-catalyzed cross-coupling reactions. This compound is a derivative of 5-bromonicotinic acid (BrnicH) which has been widely used in the last decade to obtain MOF materials with unique luminescence, magnetism, catalysis, and adsorption through assembling with lanthanide ions and transition metal ions, such as Cu(II), Co(II), Cd(II), Zn(II), and Pb(II)[1-2].

Synthesis

To an ice-cooled suspension of 5-bromo nicotinic acid (1.6g, 7.9 mmol) in diethyl ether (20ml), a solution of diazomethane in diethyl ether was added dropwise with stirring until the mixture remained yellow. The mixture was stirred for additional 15min (hood!), and the volatile compounds were removed by distillation in vaeuo. Finally, Methyl 5-bromonicotinate was obtained after purification[2].

References

[1] WENJIE LI . Syntheses, crystal structures, and properties of new metal–5-bromonicotinate coordination polymers[J]. Journal of Solid State Chemistry, 2015. DOI:10.1016/j.jssc.2015.01.002.
[2] Bracher, F., Papke, T. Total syntheses and antimicrobial activities of pyridine alkaloids from Rubiaceae. Monatsh Chem 126, 805–809 (1995). https://doi.org/10.1007/BF00807174

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