2-Chloro-4-fluoroaniline
[CAS# 2106-02-7]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoroaniline series
• Name: 2-Chloro-4-fluoroaniline
• Synonyms: 2-Chloro-4-fluorobenzenamine
• Molecular Formula: C₆H₅ClFN
• Molecular Weight: 145.56
• CAS Registry Number: 2106-02-7
• EC Number: 218-282-0
• SMILES: C1=CC(=C(C=C1F)Cl)N

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.219 g/mL (Expl.)
• Index of Refraction: 1.570, Calc.^*, 1.554 (Expl.)
• Boiling Point: 192.0±0.0 ºC (760 mmHg), Calc.^*, 192 ºC (Expl.)
• Flash Point: 98.3±0.0 ºC, Calc.^*, 98 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335-H373
• Precautionary 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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2-Chloro-4-fluoroaniline is an important aromatic amine compound that features both a chloro group at the 2-position and a fluoro group at the 4-position of the benzene ring. This chemical structure is representative of a class of halogenated aniline derivatives, which have garnered significant attention due to their diverse applications in organic synthesis, materials science, and pharmaceutical development.

The discovery of 2-chloro-4-fluoroaniline, like many halogenated aromatic compounds, was likely motivated by the growing interest in the functionalization of aniline derivatives. Aniline itself, discovered in the early 19th century, has been widely used as a building block in the synthesis of dyes, drugs, and other chemical products. The introduction of halogen atoms such as chlorine and fluorine at specific positions on the aromatic ring provides unique electronic and steric properties, which enhance the reactivity of the compound and open up a wide range of synthetic possibilities.

2-Chloro-4-fluoroaniline is typically synthesized through halogenation reactions involving fluorination and chlorination of aniline. The process can be performed using standard electrophilic aromatic substitution reactions, where suitable reagents are employed to selectively introduce chlorine and fluorine at the desired positions on the aromatic ring. The resulting compound is typically characterized using techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and infrared (IR) spectroscopy, which provide detailed information on its chemical structure.

One of the most prominent applications of 2-chloro-4-fluoroaniline lies in the field of pharmaceutical chemistry. Halogenated anilines, including this compound, are frequently used as intermediates in the synthesis of various bioactive molecules. For instance, 2-chloro-4-fluoroaniline can be employed in the preparation of more complex molecules that exhibit anti-inflammatory, antimicrobial, and anticancer activities. Fluorine, in particular, is a valuable substituent in drug design due to its electronegativity, which can influence the compound’s metabolic stability and binding affinity to biological targets.

In addition to its pharmaceutical uses, 2-chloro-4-fluoroaniline is an important intermediate in the synthesis of dyes and pigments. The unique combination of chlorine and fluorine atoms on the aromatic ring can impart specific color properties and stability to the final product. As such, this compound can serve as a precursor for the development of various industrial dyes used in textiles, plastics, and coatings.

Moreover, 2-chloro-4-fluoroaniline has applications in materials science, particularly in the development of organic semiconductors and electronic materials. The presence of halogen atoms can modulate the electronic properties of the aromatic ring, making the compound useful in the design of materials with specific conductivity or optoelectronic properties. For example, derivatives of 2-chloro-4-fluoroaniline are being explored in the development of organic light-emitting diodes (OLEDs) and other organic electronic devices, where their unique electronic characteristics play a critical role in device performance.

2-Chloro-4-fluoroaniline is also utilized in the synthesis of agrochemicals. The functionalization of aniline derivatives with halogen atoms can modify their biological activity, making them suitable for the development of herbicides, fungicides, and insecticides. Halogenated anilines are often more stable and selective in their action, which is important for the efficacy and safety of agricultural chemicals.

In summary, 2-chloro-4-fluoroaniline is a versatile compound with a wide range of applications in the pharmaceutical, materials, and agrochemical industries. Its halogenated structure enhances its reactivity and makes it a valuable intermediate for the synthesis of bioactive compounds, dyes, and organic electronic materials. As research continues into the applications of halogenated aniline derivatives, 2-chloro-4-fluoroaniline is expected to play a crucial role in the development of new chemical products and technologies.