5-Bromonicotinic acid Chemical Properties

Melting point:

178-180 °C(lit.)

Boiling point:

259.67°C (rough estimate)

Density 

1.7477 (rough estimate)

vapor pressure 

0.01Pa at 25℃

refractive index 

1.6120 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

3.08±0.10(Predicted)

color 

White to yellow-gray or light brown

BRN 

115854

InChI

InChI=1S/C6H4BrNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3H,(H,9,10)

InChIKey

FQIUCPGDKPXSLL-UHFFFAOYSA-N

SMILES

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

LogP

1.17-1.29 at 23.5℃ and pH6.4

CAS DataBase Reference

20826-04-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

QT0868000

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:5-Bromonicotinic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Bromonicotinic acid Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

5-Bromopyridine-3-carboxylic acid (5-bromonicotinic acid) was used in the synthesis of 3-guanidinomethyl-5-iodopyridine.

Reactions

5-Bromonicotinic acid could used as starting material to synthesize 3-guanidinomethyl-5-iodopyridine. It is also used to prepare four novel multifunctional coordination compounds with different lanthanide(III) ions (Dy, Tb, Yb, and Nd). These materials possess different structures and dimensionalities and show interesting magnetic and luminescence properties, as well as a complete absence of cytotoxicity both in cancer and non-cancer Caco-2 cells[1-2].

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 2381, 1948 DOI: 10.1021/ja01187a020

Purification Methods

The acid is recrystallised from H2O and then from EtOH using charcoal. The amide has m 219-219.5o (from aqueous EtOH), and the methyl ester, prepared by addition of ethereal diazomethane, can be purified by sublimation in a vacuum and has m 98-99o. The acid chloride also can be sublimed in vacuo and has m 74-75o and gives the methyl ester in MeOH. [Graf J Prakt Chem 138 244 1933, Bachman & Micucci J Am Chem Soc 70 2381 1948, Garcia et al. J Am Chem Soc 82 4430 1960, Misic-Vokovic et al. J Chem Soc 34 1978, Beilstein 22/2 V 181.]

References

[1] Vaidyanathan G, et al. Iodopyridine-for-iodobenzene substitution for use with low molecular weight radiopharmaceuticals: application to m-iodobenzylguanidine. Bioconjugate Chemistry, 1998; 9: 758–764.
[2] Ruiz C, et al. Multifunctional coordination compounds based on lanthanide ions and 5-bromonicotinic acid: magnetic, luminescence and anti-cancer properties. CrystEngComm, 2019; 21: 3881-3890.

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