3-Bromo-5-fluoro-2-methylaniline
[CAS# 502496-36-8]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoroaniline series
• Name: 3-Bromo-5-fluoro-2-methylaniline
• Synonyms: 3-Bromo-5-fluoro-2-methylphenylamine; 3-Bromo-5-fluoro-2-methylbenzenamine
• Molecular Formula: C₇H₇BrFN
• Molecular Weight: 204.04
• CAS Registry Number: 502496-36-8
• EC Number: 963-238-2
• SMILES: CC1=C(C=C(C=C1Br)F)N

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 258.9±35.0 °C 760 mmHg (Calc.)^*
• Flash point: 110.4±25.9 °C (Calc.)^*
• Index of refraction: 1.585 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: 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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

3-Bromo-5-fluoro-2-methylaniline is an organic compound that belongs to the class of substituted aniline derivatives. Aniline (C6H5NH2) is a simple aromatic amine where the amine group (-NH2) is attached to a benzene ring. In this case, the benzene ring is further substituted with a bromine atom at the 3-position, a fluorine atom at the 5-position, and a methyl group (-CH3) at the 2-position.

The presence of these substituents introduces specific electronic and steric effects that significantly influence the chemical and physical properties of the compound.

The bromine atom at the 3-position is an electron-withdrawing group due to its electronegativity. This tends to reduce the electron density on the benzene ring, making the molecule more susceptible to electrophilic substitution reactions. Additionally, the presence of the bromine atom can impact the reactivity of the amine group in subsequent reactions, such as nucleophilic aromatic substitution or coupling reactions.

The fluorine atom at the 5-position also introduces an electron-withdrawing effect due to its high electronegativity. This can further decrease the electron density on the aromatic ring and increase the electrophilicity of the ring, making it more reactive toward electrophilic substitution. Moreover, fluorine substitution in aromatic compounds often enhances their stability and lipophilicity, which is important for biological activity and material properties.

The methyl group at the 2-position is an electron-donating group through inductive effects. This tends to increase the electron density on the aromatic ring and can influence the reactivity of the molecule in different ways. The methyl group also introduces steric hindrance in the vicinity of the amine group, which can affect the spatial arrangement of the molecule and its ability to interact with other chemical entities.

Due to these structural modifications, 3-bromo-5-fluoro-2-methylaniline exhibits a unique set of properties that make it useful in various chemical and pharmaceutical applications. For example, as a functionalized aniline derivative, it can serve as a building block for the synthesis of more complex organic molecules. The compound can undergo reactions such as electrophilic aromatic substitution, nucleophilic aromatic substitution, and cross-coupling reactions, allowing the synthesis of a wide range of substituted aromatic compounds.

In addition to its synthetic utility, 3-bromo-5-fluoro-2-methylaniline may have potential biological activity. Many aniline derivatives, especially those with halogen (fluorine and bromine) and methyl groups, are of interest in medicinal chemistry due to their potential antimicrobial, anticancer, and anti-inflammatory activities. The electron-withdrawing nature of the bromine and fluorine atoms may enhance the compound’s ability to interact with biological targets, such as enzymes or receptors, contributing to its pharmacological profile.

Furthermore, the compound could have applications in the field of materials science. For example, substituted aniline derivatives are often used in the synthesis of organic semiconductors, dyes, and pigments. The electron-donating and electron-withdrawing properties of the various substituents can influence the electronic and optical properties of the material, making it suitable for applications in organic electronics, such as organic light-emitting diodes (OLEDs) and organic solar cells.

In summary, 3-bromo-5-fluoro-2-methylaniline is a versatile compound with applications in organic synthesis, medicinal chemistry, and materials science. Its unique combination of halogen and methyl substituents on the aniline ring provides it with a range of electronic and steric properties that can be exploited in the development of new chemical entities and functional materials.