5-Bromo-2-nitropyridine
[CAS# 39856-50-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
• Name: 5-Bromo-2-nitropyridine
• Molecular Formula: C₅H₃BrN₂O₂
• Molecular Weight: 202.99
• CAS Registry Number: 39856-50-3
• EC Number: 609-748-8
• SMILES: C1=CC(=NC=C1Br)[N+](=O)[O-]

Properties

• Density: 1.8±0.1 g/cm³ Calc.^*
• Melting point: 148 - 150 °C (Expl.)
• Boiling point: 292.3±20.0 °C 760 mmHg (Calc.)^*
• Flash point: 130.6±21.8 °C (Calc.)^*
• Index of refraction: 1.614 (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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

5-Bromo-2-nitropyridine is a chemical compound that belongs to the class of halogenated nitropyridines. It is used primarily in the synthesis of other organic compounds, especially in the pharmaceutical and agrochemical industries, due to its reactive functional groups. The compound contains both a bromine atom and a nitro group attached to the pyridine ring, which significantly influences its reactivity and makes it a valuable building block in chemical synthesis.

The discovery and development of 5-bromo-2-nitropyridine stem from the need for compounds that can serve as intermediates in the synthesis of bioactive molecules, particularly those with potential pharmacological activity. The presence of both bromine and nitro groups in the structure enables this compound to participate in various chemical reactions, such as nucleophilic substitution and coupling reactions, which are commonly used to construct more complex molecules.

In particular, the bromo and nitro functionalities in 5-bromo-2-nitropyridine make it suitable for reactions like Suzuki couplings, nucleophilic aromatic substitution, and other cross-coupling reactions. These reactions are essential in the formation of various carbon-carbon bonds, which are fundamental in the synthesis of medicinal compounds, agrochemicals, and advanced materials.

One of the primary applications of 5-bromo-2-nitropyridine is as an intermediate in the synthesis of pharmaceuticals. For example, it can be used in the synthesis of pyridine-based compounds with antimicrobial, anticancer, or anti-inflammatory properties. Due to its structural features, 5-bromo-2-nitropyridine can undergo selective reactions that allow for the creation of a wide range of functionalized pyridine derivatives, which are valuable in drug design.

In addition to pharmaceutical applications, this compound is also used in the agrochemical industry for the development of plant protection agents. Pyridine derivatives, including those containing bromine and nitro groups, are often investigated for their insecticidal and herbicidal properties. The ability to modify the functional groups on the pyridine ring allows researchers to fine-tune the properties of these compounds, making them more effective in pest control and agricultural applications.

The reactivity of 5-bromo-2-nitropyridine, especially its potential for electrophilic substitution reactions, also makes it useful in material science. It can be incorporated into various organic materials that exhibit electronic or optical properties, contributing to the development of advanced materials for use in electronics, sensors, and other high-tech applications.

Despite its utility in synthesis and applications in diverse fields, 5-bromo-2-nitropyridine, like many other halogenated compounds, must be handled with care due to its potentially hazardous nature. The nitro group, in particular, can contribute to the toxicity of the compound, making it important to observe proper safety protocols during its use in laboratory or industrial settings.

In conclusion, 5-bromo-2-nitropyridine is a valuable chemical intermediate that plays a crucial role in the synthesis of a wide range of bioactive molecules, pharmaceuticals, and agrochemicals. Its reactivity, owing to the presence of both a bromine atom and a nitro group, allows for diverse chemical reactions that are essential in the construction of complex molecules. The compound's applications span multiple industries, including drug development and agriculture, highlighting its versatility as a synthetic building block.

References

2005. FT-Raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 62(1-3).
DOI: 10.1016/j.saa.2004.11.016

2022. Methemoglobinemia and Delayed Encephalopathy After 5-Bromo-2-Nitropyridine Poisoning: A Rare Case Report. Frontiers in Public Health, 10.
DOI: 10.3389/fpubh.2022.942003

2023. Development of novel palbociclib-based CDK4/6 inhibitors exploring the back pocket behind the gatekeeper. Investigational New Drugs, 41(5).
DOI: 10.1007/s10637-023-01385-0