4-Amino-2-(trifluoromethyl)benzonitrile
[CAS# 654-70-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 4-Amino-2-(trifluoromethyl)benzonitrile
• Synonyms: 5-Amino-2-cyanobenzotrifluoride
• Molecular Formula: C₈H₅F₃N₂
• Molecular Weight: 186.14
• CAS Registry Number: 654-70-6
• EC Number: 700-293-1
• SMILES: C1=CC(=C(C=C1N)C(F)(F)F)C#N

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 141-145 °C (Expl.)
• Index of Refraction: 1.500, Calc.^*
• Boiling Point: 294.5±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 131.9±27.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H302-H311-H315-H317-H319-H330-H335
• Safety Statements: P260-P261-P262-P264-P264+P265-P270-P271-P272-P280-P284-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P319-P320-P321-P330-P332+P317-P333+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	2	H330
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Amino-2-(trifluoromethyl)benzonitrile is an organic compound with the chemical formula C8H6F3N. It is an aromatic nitrile that features both an amino group and a trifluoromethyl group attached to a benzene ring. This compound is a valuable intermediate in the field of organic synthesis, particularly in the pharmaceutical, agricultural, and materials industries due to its unique chemical properties.

The discovery of 4-amino-2-(trifluoromethyl)benzonitrile traces back to the development of aromatic compounds with enhanced properties. The trifluoromethyl group is known for its ability to modify the chemical reactivity of aromatic compounds, often leading to compounds with improved stability, solubility, and bioactivity. This compound was likely identified as part of a broader effort to explore and develop fluorinated aromatic compounds with diverse applications. Its synthesis involves standard methods of aromatic substitution, where the amino and trifluoromethyl groups are introduced onto the benzene ring.

One of the primary applications of 4-amino-2-(trifluoromethyl)benzonitrile is in the synthesis of pharmaceuticals and agrochemicals. The trifluoromethyl group is of particular interest in drug development because it can enhance the biological activity of molecules, as well as improve their metabolic stability and solubility. The compound serves as a key intermediate in the preparation of drugs that require precise modulation of their chemical properties for optimal effectiveness. In pharmaceutical chemistry, trifluoromethylated compounds are often designed to interact with biological targets, including receptors or enzymes, with greater selectivity and potency.

The amino group in 4-amino-2-(trifluoromethyl)benzonitrile also makes it useful in a variety of synthetic reactions. It can be readily functionalized to introduce new chemical groups, which further expands its versatility as a building block for more complex molecules. For example, this compound can be used in the synthesis of heterocyclic compounds, where the amino group participates in nucleophilic substitution reactions. This ability to undergo further chemical modifications has led to the development of a wide range of compounds with diverse biological activities, making it a valuable tool in medicinal chemistry.

In the agricultural industry, 4-amino-2-(trifluoromethyl)benzonitrile has been explored for use in the development of new pesticides and herbicides. The trifluoromethyl group is known for imparting certain desirable properties to agrochemicals, such as increased effectiveness at lower doses and improved resistance to environmental degradation. As such, this compound has potential applications in the design of more efficient and sustainable agricultural chemicals, contributing to crop protection and food production.

Additionally, 4-amino-2-(trifluoromethyl)benzonitrile finds utility in materials science, particularly in the development of specialty polymers and coatings. The presence of both an amino group and a trifluoromethyl group enables this compound to participate in polymerization reactions, where it can contribute to the creation of high-performance materials with enhanced chemical resistance, stability, and durability. These materials are used in a variety of applications, from electronics to coatings for harsh environmental conditions.

Despite its many useful applications, 4-amino-2-(trifluoromethyl)benzonitrile must be handled with care due to its potential toxicity and environmental impact. As with other nitriles, the compound can release harmful gases upon combustion or decomposition, and prolonged exposure may pose risks to human health. Therefore, appropriate safety protocols should be followed when working with this compound, particularly in industrial or laboratory settings.

In conclusion, 4-amino-2-(trifluoromethyl)benzonitrile is a versatile chemical with significant applications in the fields of pharmaceuticals, agrochemicals, and materials science. Its unique combination of functional groups makes it a valuable building block for the synthesis of complex molecules with improved properties, and its potential in drug and agrochemical development continues to be explored. Ongoing research into its applications will likely lead to new innovations in these industries, further demonstrating the compound’s importance.

References

2012. Discovery of 2-(4-cyano-3-trifluoromethylphenyl amino)-4-(4-quinazolinyloxy)-6-piperazinyl(piperidinyl)-s-triazines as potential antibacterial agents. Medicinal Chemistry Research, 21(11).
DOI: 10.1007/s00044-011-9950-4