5-Bromonicotinic acid
[CAS# 20826-04-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other protected amino acids
• Name: 5-Bromonicotinic acid
• Synonyms: 5-Bromo-3-pyridinecarboxylic acid
• Molecular Formula: C₆H₄BrNO₂
• Molecular Weight: 202.01
• CAS Registry Number: 20826-04-4
• EC Number: 244-065-5
• SMILES: C1=C(C=NC=C1Br)C(=O)O

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 178-184 °C (expl.)
• Index of Refraction: 1.617, Calc.^*
• Boiling Point: 328.5±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 152.5±23.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

5-Bromonicotinic acid is a halogenated derivative of nicotinic acid, a well-known compound that plays a vital role in the synthesis of coenzymes, particularly nicotinamide adenine dinucleotide (NAD), which is essential for various biochemical reactions. The incorporation of a bromine atom at the 5-position of the pyridine ring in nicotinic acid significantly alters the chemical and biological properties of the molecule. This modification enhances the compound's versatility in medicinal chemistry, agrochemical applications, and materials science.

The discovery of 5-bromonicotinic acid stems from the broader interest in halogenated pyridine derivatives, which have long been recognized for their bioactivity and utility in drug discovery. The introduction of the bromine atom at the 5-position offers unique advantages, such as improved stability, enhanced lipophilicity, and the ability to modulate interactions with biological targets, making it a promising candidate for various applications.

One of the key areas where 5-bromonicotinic acid has been studied is in medicinal chemistry. Its halogenated structure makes it an attractive scaffold for the development of bioactive compounds. Specifically, 5-bromonicotinic acid derivatives have been investigated for their potential to interact with certain enzymes and receptors. The compound has shown promise as a precursor in the synthesis of potential anti-cancer agents, with studies suggesting that it could be used to develop compounds that inhibit specific kinases involved in tumor cell proliferation. Moreover, 5-bromonicotinic acid derivatives have also been evaluated for their neuroprotective properties, suggesting their potential role in treating neurodegenerative diseases such as Alzheimer's and Parkinson's diseases.

In addition to its medicinal applications, 5-bromonicotinic acid is being explored in the field of agrochemicals. Nicotinic acid derivatives, including 5-bromonicotinic acid, have demonstrated insecticidal and pesticidal properties, which make them useful for developing new crop protection agents. The compound's ability to interact with nicotinic receptors in pests, disrupting their nervous systems, is a key mechanism that underlies its insecticidal action. Researchers are working to enhance the selectivity and potency of 5-bromonicotinic acid derivatives, aiming to create more efficient and environmentally friendly pesticides.

Another application of 5-bromonicotinic acid lies in materials science, particularly in the development of organic semiconductors and photovoltaic materials. The halogenated pyridine structure provides desirable electronic properties, such as improved charge transport and stability, which are crucial for the performance of organic electronic devices. 5-Bromonicotinic acid and its derivatives have been studied for their potential use in organic light-emitting diodes (OLEDs), organic solar cells, and other organic electronic devices, contributing to the growing field of organic electronics.

The synthesis of 5-bromonicotinic acid generally involves the bromination of nicotinic acid under controlled conditions, ensuring the selective incorporation of the bromine atom at the 5-position of the pyridine ring. This process can be further optimized to yield high-purity products suitable for use in pharmaceutical and industrial applications.

In conclusion, 5-bromonicotinic acid is a versatile compound with a range of potential applications across medicinal chemistry, agrochemicals, and materials science. Its ability to interact with biological targets, combined with its unique electronic properties, makes it a valuable building block for the development of new therapeutic agents, pesticides, and electronic materials. Ongoing research into the synthesis, reactivity, and biological activity of 5-bromonicotinic acid will likely continue to expand its utility in various fields of science and industry.

References

2007. Synthesis of Diorganotin Esters of 5-Bromonicotinic Acid: X-ray Crystal Structure of Polymeric 5-Bromonicotinatodiorganotin. Journal of Inorganic and Organometallic Polymers and Materials, 17(4).
DOI: 10.1007/s10904-007-9116-5

2022. A quantitative high-throughput screen identifies compounds that lower expression of the SCA2-and ALS-associated gene ATXN2. The Journal of Biological Chemistry, 298(8).
DOI: 10.1016/j.jbc.2022.102228

2018. One-step labelling of a novel small-molecule peptide with astatine-211: preliminary evaluation in vitro and in vivo. Journal of Radioanalytical and Nuclear Chemistry, 316(1).
DOI: 10.1007/s10967-018-5780-x