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HomeProduct name list5-Bromonicotinic acid

5-Bromonicotinic acid

Synonym(s):5-Bromonicotinic acid;5-Bromopyridine-3-carboxylic acid

  • CAS NO.:20826-04-4
  • Empirical Formula: C6H4BrNO2
  • Molecular Weight: 202.01
  • MDL number: MFCD00009783
  • EINECS: 244-065-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-15 19:00:21
5-Bromonicotinic acid Structural

What is 5-Bromonicotinic acid?

Chemical properties

Light yellow Cryst

The Uses of 5-Bromonicotinic acid

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.

Properties of 5-Bromonicotinic acid

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)
CAS DataBase Reference 20826-04-4(CAS DataBase Reference)

Safety information for 5-Bromonicotinic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 5-Bromonicotinic acid

InChIKey FQIUCPGDKPXSLL-UHFFFAOYSA-N
SMILES C1=NC=C(Br)C=C1C(O)=O

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