3-Bromo-2-fluoroaniline
[CAS# 58534-95-5]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoroaniline series
• Name: 3-Bromo-2-fluoroaniline
• Synonyms: 3-Bromo-2-fluorophenylamine
• Molecular Formula: C₆H₅BrFN
• Molecular Weight: 190.01
• CAS Registry Number: 58534-95-5
• EC Number: 820-692-5
• SMILES: C1=CC(=C(C(=C1)Br)F)N

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 227.5±20.0 ºC 760 mmHg (Calc.)^*
• Flash point: 91.4±21.8 ºC (Calc.)^*
• Index of refraction: 1.597 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H302-H311-H312-H315-H319-H331-H332-H335
• Precautionary Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-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
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H301

Discovory and Applicatios

3-Bromo-2-fluoroaniline is an aromatic compound featuring a benzene ring with a bromine (Br) atom at the 3-position, a fluorine (F) atom at the 2-position, and an amine group (-NH2) at the 1-position. This structure places the amine group, a strong electron-donating group, at the para position relative to the fluorine and bromine substituents, which are electron-withdrawing groups. The combination of these substituents imparts specific reactivity to the molecule, making it useful in various synthetic applications.

The synthesis of 3-bromo-2-fluoroaniline typically involves the selective halogenation of aniline, a common method in organic chemistry. The bromine and fluorine atoms are introduced via electrophilic aromatic substitution reactions. These halogen atoms are placed at the 3- and 2-positions of the aniline ring, respectively, typically using bromine and a fluorinating agent. The nitro group, commonly used as an electrophile in such reactions, can be converted into a fluoro- or bromo-substituted aromatic structure. The order of substitution is crucial for the selective placement of the halogens, as the presence of the amine group influences the regioselectivity of the halogenation.

3-Bromo-2-fluoroaniline has several important applications in the synthesis of pharmaceutical and agrochemical compounds. The presence of both halogens and an amine group on the aromatic ring creates opportunities for further chemical modifications. These include coupling reactions with other electrophiles to form biaryl compounds, which are common in drug design. Additionally, the compound’s ability to undergo nucleophilic substitution reactions makes it useful as a precursor to a variety of functionalized organic compounds.

In the field of medicinal chemistry, 3-bromo-2-fluoroaniline and its derivatives are studied for their biological activities. The halogen atoms, especially the fluorine, can modulate the lipophilicity, electronic properties, and metabolic stability of a molecule, which are important factors in the development of pharmaceutical agents. For example, fluorine substitution often increases a molecule's binding affinity for biological targets, such as enzymes or receptors, and improves its pharmacokinetic properties, including absorption and bioavailability.

In particular, 3-bromo-2-fluoroaniline derivatives have been investigated as potential intermediates in the synthesis of kinase inhibitors, anti-inflammatory agents, and other bioactive molecules. The structure of the molecule, with its ability to donate electrons via the amine group and accept electrons via the halogens, could also influence its interactions with metal ions or other biomolecules, making it a candidate for further exploration in drug development.

Moreover, 3-bromo-2-fluoroaniline is valuable in materials science, particularly in the synthesis of organic semiconductors and light-emitting devices. The combination of halogens and amines in the molecule can alter the electronic properties of conjugated polymers or small molecules, which are essential in the development of advanced materials for electronic applications. For example, fluorine can improve the thermal stability and solubility of organic semiconductors, while bromine may enhance their ability to form stable charge-transporting layers.

The reactivity of 3-bromo-2-fluoroaniline also makes it an important intermediate in the synthesis of other complex organic compounds. By introducing different functional groups to the molecule through electrophilic substitution or nucleophilic addition, it is possible to generate a wide range of derivatives with diverse properties and applications. The compound is thus considered a versatile building block in both academic research and industrial applications.

In conclusion, 3-bromo-2-fluoroaniline is an important aromatic compound that serves as a useful intermediate in organic synthesis. Its unique combination of halogen and amine substituents provides a versatile platform for the development of pharmaceuticals, agrochemicals, and advanced materials. Its reactivity and ability to undergo selective substitutions make it a valuable starting material for further chemical modifications. As research continues, 3-bromo-2-fluoroaniline and its derivatives will likely find expanding roles in various fields of chemistry and material science.