5-Bromo-2-methoxy-3-nitro-4-picoline
[CAS# 884495-14-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
• Name: 5-Bromo-2-methoxy-3-nitro-4-picoline
• Synonyms: 5-Bromo-2-methoxy-4-methyl-3-nitropyridine
• Molecular Formula: C₇H₇BrN₂O₃
• Molecular Weight: 247.05
• CAS Registry Number: 884495-14-1
• EC Number: 848-711-2
• SMILES: CC1=C(C(=NC=C1Br)OC)[N+](=O)[O-]

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*, 1.576 - 1.696 g/mL (Expl.)
• Boiling point: 302.8±37.0 °C 760 mmHg (Calc.)^*
• Flash point: 136.9±26.5 °C (Calc.)^*
• Index of refraction: 1.578 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

5-Bromo-2-methoxy-3-nitro-4-picoline is a halogenated, nitro-substituted derivative of picoline, a methylated pyridine. Picoline derivatives, including this compound, are of significant interest in organic chemistry due to their diverse reactivity and potential applications in various fields. This particular compound features a bromine atom, a methoxy group, and a nitro group at specific positions on the picoline ring, each contributing to its unique chemical behavior.

The compound is synthesized through typical methods for halogenated nitropyridine derivatives, which generally involve selective substitution reactions. These reactions can be initiated under specific conditions, allowing for the controlled introduction of the halogen, methoxy, and nitro groups at the desired positions on the aromatic ring. The synthesis of such compounds is of particular interest for researchers exploring new ways to modify pyridine derivatives for various applications.

5-Bromo-2-methoxy-3-nitro-4-picoline's primary applications lie in the fields of organic synthesis and pharmaceutical chemistry. Its reactivity makes it a useful intermediate for the synthesis of other complex organic molecules. For instance, the bromine and nitro groups present in the compound can participate in nucleophilic substitution reactions, leading to the formation of new chemical entities. Additionally, the methoxy group can undergo electrophilic aromatic substitution, further enhancing the compound's versatility.

In pharmaceutical chemistry, pyridine derivatives like 5-Bromo-2-methoxy-3-nitro-4-picoline are valuable in the development of bioactive compounds. Many bioactive molecules, including those with antimicrobial, anti-inflammatory, or anticancer properties, contain pyridine or substituted pyridine rings. As such, this compound may serve as a precursor or building block for drug discovery, particularly for compounds that require specific functional group placements for activity.

Furthermore, this compound has been studied in the context of materials science and as a potential candidate for various catalytic processes. The functional groups attached to the pyridine ring can influence the compound’s electron density, making it suitable for use in catalytic reactions or as a ligand in coordination chemistry. The compound’s electron-deficient nitro group and electron-donating methoxy group, along with the halogenated bromine atom, provide a range of reactivity that could be harnessed in novel catalytic cycles or in the synthesis of organic materials with specific electronic or optical properties.

In summary, 5-Bromo-2-methoxy-3-nitro-4-picoline is an important intermediate in organic synthesis, with applications in pharmaceutical development, materials science, and catalysis. Its unique combination of functional groups makes it a versatile building block for the creation of a wide array of compounds. As a result, it continues to be of interest for its potential role in advancing chemical research and the development of new materials and bioactive substances.

References

2020. Synthesis of ABBV-744. Synfacts, 2020.
DOI: 10.1055/s-0040-1707095