4-Fluoroaniline
[CAS# 371-40-4]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoroaniline series
• Name: 4-Fluoroaniline
• Synonyms: 1-Amino-4-fluorobenzene; 4-Fluorobenzenamine
• Molecular Formula: C₆H₆FN
• Molecular Weight: 111.12
• CAS Registry Number: 371-40-4
• EC Number: 206-735-5
• SMILES: C1=CC(=CC=C1N)F

Properties

• Density: 1.1586
• Melting point: -1.9 ºC
• Boiling point: 187 ºC
• Refractive index: 1.5385-1.5405
• Flash point: 81 ºC
• Water solubility: 33 g/L (20 ºC)

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H312-H314-H317-H318-H319-H332-H372-H373-H400-H410-H411
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	4	H332
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H311
Germ cell mutagenicity	Muta.	2	H341

• Transport Information: UN 2944

Discovory and Applicatios

4-Fluoroaniline, a derivative of aniline, was first synthesized in the late 19th century through the nitration and reduction of 4-nitroaniline. The introduction of the fluorine atom onto the benzene ring significantly altered the chemical properties of the compound, enhancing its versatility and applicability in various industries. Initially discovered for its synthetic utility in organic chemistry, 4-fluoroaniline has since found widespread applications across pharmaceuticals, agrochemicals, dyes, and materials science. Its synthesis marked a pivotal moment in the development of fluorinated compounds, which have become integral components in modern chemical synthesis and industrial processes.

4-Fluoroaniline serves as a crucial building block in the synthesis of pharmaceutical compounds, particularly those with fluorinated motifs. Its incorporation into drug molecules can enhance bioavailability, metabolic stability, and target specificity, leading to improved therapeutic outcomes. Fluorinated pharmaceuticals are known for their resistance to metabolic degradation, making 4-fluoroaniline an essential intermediate in the development of long-lasting and efficacious drugs. Many drugs containing fluorine atoms, such as fluoroquinolone antibiotics and selective serotonin reuptake inhibitors (SSRIs), rely on 4-fluoroaniline as a key precursor. By strategically introducing fluorine atoms into drug structures, medicinal chemists can fine-tune pharmacological properties like lipophilicity and protein binding affinity, resulting in optimized drug candidates.

4-Fluoroaniline is utilized in the synthesis of various agrochemicals, including herbicides, insecticides, and fungicides. Its incorporation into pesticide formulations enhances efficacy and environmental persistence, allowing for targeted pest control with reduced environmental impact. By introducing fluorine functionality, agrochemical manufacturers can develop compounds with improved stability, bioactivity, and selectivity, contributing to sustainable agricultural practices.

The chemical versatility of 4-fluoroaniline makes it an essential component in the synthesis of dyes and pigments. Its fluorinated derivative exhibits unique color properties and lightfastness, making it desirable for producing vibrant and durable colorants used in textiles, plastics, and coatings. By modifying the molecular structure of 4-fluoroaniline, dye chemists can engineer custom colors with specific dyeing properties, catering to diverse industrial applications.

4-Fluoroaniline plays a crucial role in polymer chemistry, where it is used as a monomer for synthesizing fluorinated polymers with enhanced mechanical, thermal, and chemical properties. Fluorinated polymers exhibit exceptional resistance to solvents, acids, and extreme temperatures, making them valuable materials for aerospace, automotive, and electronic applications. By incorporating 4-fluoroaniline into polymer chains, materials scientists can engineer polymers with tailored properties to meet specific performance requirements. The surface functionalization of materials with fluorinated groups is essential for imparting hydrophobicity, oleophobicity, and low surface energy. 4-Fluoroaniline derivatives are employed in surface treatment processes to modify the surface properties of substrates like glass, metals, and polymers. This surface modification enhances durability, corrosion resistance, and adhesion, making treated materials suitable for a wide range of industrial applications, including coatings, adhesives, and electronic components.

References

2023. SNH Arylamination of 5(6,7,8)-nitroquinoline N-oxides. Chemistry of Heterocyclic Compounds, 59(5).
DOI: 10.1007/s10593-023-03193-z

2023. Adsorption and Co-adsorption of 2,4-Difluoroaniline and Copper (II) Using Nickel-Manganese Ferrite Magnetic Biochar Derived from Orange Peel. Water, Air, & Soil Pollution, 234(6).
DOI: 10.1007/s11270-023-06445-y

2023. Theoretical investigation of NLO and spectroscopic properties of halogenated aniline. Optical and Quantum Electronics, 55(12).
DOI: 10.1007/s11082-023-05132-w