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Methyl 5-bromonicotinate

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Methyl 5-bromonicotinate Basic information

Product Name:
Methyl 5-bromonicotinate
Synonyms:
  • 5-BROMO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER
  • 5-BROMOPYRIDINE-3-CARBOXYLIC ACID METHYL ESTER
  • 5-BROMO NICOTINIC ACID METHYL ESTER
  • METHYL 5-BROMONICOTINATE
  • METHYL 5-BROMOPYRIDINE-3-CARBOXYLATE
  • METHYL 3-BROMO-5-PYRIDINECARBOXYLATE
  • BUTTPARK 37\04-20
  • 5-Bromonictinic acid ethyl ester
CAS:
29681-44-5
MF:
C7H6BrNO2
MW:
216.03
EINECS:
627-974-5
Product Categories:
  • blocks
  • Bromides
  • Carboxes
  • Pyridines
Mol File:
29681-44-5.mol
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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)
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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

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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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