5-Bromonicotinamide
[CAS# 28733-43-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 5-Bromonicotinamide
• Synonyms: 5-Bromo-3-pyridinecarboxamide
• Molecular Formula: C₆H₅BrN₂O
• Molecular Weight: 201.02
• CAS Registry Number: 28733-43-9
• EC Number: 626-875-4
• SMILES: C1=C(C=NC=C1Br)C(=O)N

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 219-232 °C (Expl.)
• Index of Refraction: 1.614, Calc.^*
• Boiling Point: 315.5±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 144.6±23.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

5-Bromonicotinamide is a chemical compound belonging to the class of pyridine derivatives. It has the molecular formula C₆H₆BrN₁O, and its structure consists of a pyridine ring (a six-membered aromatic ring containing one nitrogen atom) with a bromine atom at the 5-position and an amide group (-CONH₂) at the 2-position. This compound is closely related to nicotinamide, a precursor of NAD+ (nicotinamide adenine dinucleotide), which plays an essential role in cellular metabolism.

The discovery of 5-bromonicotinamide is part of the broader effort to explore the chemistry and biological properties of substituted nicotinamides. Pyridine and its derivatives, including nicotinamide and its substituted forms, have been studied extensively due to their significant biological activities. Nicotinamide derivatives, in particular, are widely recognized for their role in various biochemical pathways, including the synthesis of NAD+ and its involvement in redox reactions within cells.

5-Bromonicotinamide is synthesized through well-established organic reactions involving the bromination of nicotinamide. Bromine can be introduced into the 5-position of the pyridine ring using reagents such as NBS (N-Bromosuccinimide) or elemental bromine under suitable conditions. The compound has been used as a synthetic intermediate in the preparation of other pyridine derivatives and can undergo further chemical modifications to yield more complex compounds.

One of the key applications of 5-bromonicotinamide is in the field of medicinal chemistry, where it has been investigated for its potential pharmacological properties. Similar to other nicotinamide derivatives, 5-bromonicotinamide has been studied for its role in cellular processes such as DNA repair, cell signaling, and metabolic regulation. In particular, its ability to modulate enzymes involved in NAD+ biosynthesis has been of interest in the context of aging, cancer, and neurodegenerative diseases.

Additionally, 5-bromonicotinamide is used as a building block in the synthesis of other bioactive molecules. For example, it can be incorporated into drug discovery programs aimed at developing novel therapeutic agents targeting various diseases, including cancer and metabolic disorders. Its bromine substitution enhances its reactivity, making it a useful intermediate for coupling reactions and for introducing further functional groups at specific positions on the pyridine ring.

In the field of materials science, 5-bromonicotinamide has been investigated for its potential use in the synthesis of organic semiconductors and other functional materials. The bromine atom on the pyridine ring can influence the electronic properties of the molecule, which may be beneficial in the design of materials for electronic applications, such as organic light-emitting diodes (OLEDs) or organic photovoltaic cells.

5-bromonicotinamide also serves as a reagent in laboratory research, particularly in synthetic organic chemistry. It is employed in various reactions that require a brominated pyridine derivative, such as cross-coupling reactions, halogenation reactions, or reactions involving the formation of metal-organic complexes. The compound's functional groups make it a versatile starting material in the synthesis of a wide range of chemical products.

In analytical chemistry, 5-bromonicotinamide is sometimes used as a standard or reference compound in chromatographic techniques, including high-performance liquid chromatography (HPLC). Its distinct chemical structure allows it to be easily identified in complex mixtures, aiding in the analysis of related compounds.

The compound is commercially available from chemical suppliers and is typically used in research laboratories. It is generally stable under standard conditions, although care should be taken when handling brominated compounds due to their potential reactivity.

Overall, 5-bromonicotinamide is a valuable compound in various scientific disciplines, including medicinal chemistry, materials science, and synthetic chemistry. Its applications range from drug development to materials design, making it an important building block in the creation of bioactive molecules and functional materials. Through its established uses and well-documented chemical properties, 5-bromonicotinamide continues to contribute to advancements in multiple areas of research.

References

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DOI: 10.1055/s-0036-1589433

2016. Direct (Hetero)arylation Reactions of (Hetero)arenes as Tools for the Step- and Atom-Economical Synthesis of Biologically Active Unnatural Compounds Including Pharmaceutical Targets. Synthesis, 48(24).
DOI: 10.1055/s-0036-1588303

2003. Nicotinyl aspartyl ketones as inhibitors of caspase-3. Bioorganic & Medicinal Chemistry Letters, 13(13).
DOI: 10.1016/s0960-894x(03)00390-1