3-Bromo-2-fluoronitrobenzene
[CAS# 58534-94-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3-Bromo-2-fluoronitrobenzene
• Synonyms: 1-bromo-2-fluoro-3-nitrobenzene
• Molecular Formula: C₆H₃BrFNO₂
• Molecular Weight: 220.00
• CAS Registry Number: 58534-94-4
• EC Number: 639-357-8
• SMILES: C1=CC(=C(C(=C1)Br)F)[N+](=O)[O-]

Properties

• Density: 1.8±0.1 g/cm³ Calc.^*
• Melting point: 29 - 31 °C (Expl.)
• Boiling point: 259.1±20.0 °C 760 mmHg (Calc.)^*
• Flash point: 110.5±21.8 °C (Calc.)^*
• Index of refraction: 1.58 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335-H373
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

3-Bromo-2-fluoronitrobenzene is a halogenated aromatic compound that features three key functional groups: bromine (Br), fluorine (F), and a nitro group (NO2) on a benzene ring. This compound is of interest in both organic synthesis and material science due to its unique chemical structure, which allows for various modifications and applications. The position of the substituents on the benzene ring provides specific reactivity and selectivity in chemical reactions, making this compound useful in a range of synthetic processes.

The synthesis of 3-bromo-2-fluoronitrobenzene typically involves the selective halogenation of a nitrobenzene precursor, where bromine and fluorine are introduced at specific positions on the aromatic ring. The nitro group, being an electron-withdrawing group, influences the electron density on the ring and directs the substitution of the halogens to the meta and ortho positions, leading to the observed arrangement of the bromine at the 3-position, fluorine at the 2-position, and the nitro group at the 1-position. This selective substitution is often carried out through electrophilic aromatic substitution (EAS) reactions, which are well-established for introducing halogen and nitro groups into aromatic systems.

3-Bromo-2-fluoronitrobenzene has several potential applications in organic chemistry, particularly as an intermediate for the synthesis of more complex molecules. The halogen and nitro substitutions on the benzene ring increase the compound's reactivity, allowing for various further functionalization reactions. For example, the compound can be used as a starting material for the synthesis of substituted benzene derivatives, which are valuable in the preparation of pharmaceuticals, agrochemicals, and materials science.

In medicinal chemistry, the presence of both a bromine and a fluorine atom on the benzene ring can modify the lipophilicity, stability, and reactivity of the compound, which can influence its potential biological activity. Substituted nitrobenzenes are often studied for their ability to interact with biological targets, including enzymes, receptors, and ion channels. In particular, halogenated nitrobenzene derivatives are known for their potential as anticancer agents, as they can interact with cellular processes, such as DNA replication and cell signaling.

The fluorine atom in 3-bromo-2-fluoronitrobenzene can also influence the compound's electronic properties, making it more reactive in certain types of reactions, such as nucleophilic aromatic substitution, or in the formation of coordination complexes with metal ions. The bromine and fluorine atoms can further enhance the compound's ability to form intermolecular interactions, such as hydrogen bonding or π-π stacking, which are important in the development of functional materials.

In materials science, halogenated nitrobenzenes like 3-bromo-2-fluoronitrobenzene are explored for their potential as building blocks for organic semiconductors, light-emitting devices, or conductive polymers. The electron-deficient nature of the nitro group and the halogens may contribute to the tuning of electronic properties, which is valuable in designing materials for optoelectronic applications. The compound could also be used in the development of sensors or molecular switches, where its ability to undergo chemical transformations is important.

3-Bromo-2-fluoronitrobenzene may also find use in the synthesis of other functionalized aromatic compounds. The halogenation pattern provides a degree of molecular control, allowing for the selective addition of other groups at specific positions on the ring. This ability to direct substitution reactions makes it a valuable intermediate in complex chemical synthesis, particularly in the pharmaceutical and agrochemical industries, where fine-tuned molecular structures are often required.

In conclusion, 3-bromo-2-fluoronitrobenzene is an important halogenated aromatic compound with significant potential in organic synthesis, medicinal chemistry, and material science. Its unique combination of functional groups makes it a versatile intermediate for the preparation of more complex molecules with diverse applications. The compound's reactivity and potential for further functionalization ensure its continued relevance in both academic research and industrial applications.