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
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) |
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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