2-(1H-pyrazol-1-yl)aniline
[CAS# 54705-91-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: 2-(1H-pyrazol-1-yl)aniline
• Synonyms: 2-pyrazol-1-ylaniline
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.19
• CAS Registry Number: 54705-91-8
• EC Number: 960-623-7
• SMILES: C1=CC=C(C(=C1)N)N2C=CC=N2

Properties

• Melting Point: 48-51 °C

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
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2-(1H-pyrazol-1-yl)aniline is a noteworthy compound in organic chemistry, characterized by its unique molecular structure that combines an aniline group with a pyrazole ring. This compound has garnered attention for its versatile applications in pharmaceuticals and materials science due to its distinct chemical properties and reactivity.

The discovery of 2-(1H-pyrazol-1-yl)aniline was driven by the need to explore novel compounds with potential biological and chemical applications. The structure features an aniline moiety, which is a benzene ring with an amino group, and a pyrazole ring, which is a five-membered ring with two adjacent nitrogen atoms. This combination creates a molecule with intriguing electronic and steric properties that can be exploited in various fields.

In pharmaceuticals, 2-(1H-pyrazol-1-yl)aniline is valued for its potential as a precursor or intermediate in the synthesis of bioactive molecules. The pyrazole ring is known for its bioactivity and is often found in drugs with anti-inflammatory, antitumor, and antimicrobial properties. By incorporating the pyrazole ring into the aniline framework, researchers can modify the biological activity of the resulting compounds, making them useful in drug development and medicinal chemistry.

The compound also plays a significant role in the development of advanced materials. Its structure allows it to participate in various chemical reactions that are essential for creating complex organic materials. For instance, 2-(1H-pyrazol-1-yl)aniline can be used in the synthesis of organic semiconductors and materials for organic light-emitting diodes (OLEDs). The unique combination of aniline and pyrazole rings provides a platform for designing materials with tailored electronic and optical properties.

Moreover, 2-(1H-pyrazol-1-yl)aniline is utilized in the field of organic synthesis as a building block for constructing more complex structures. Its functional groups enable it to engage in various coupling reactions and modifications, which are crucial for producing a wide range of organic compounds with diverse applications.

In summary, 2-(1H-pyrazol-1-yl)aniline is an important compound in organic chemistry with significant applications in pharmaceuticals and materials science. Its unique structure and reactivity make it a valuable tool for developing new drugs and advanced materials, highlighting its role in both chemical research and practical applications.

References

2020. Palladium-catalyzed aminocarbonylation of aryl iodides with amines: efficient access to bidentate amide directing groups. Transition Metal Chemistry, 45(7).
DOI: 10.1007/s11243-020-00418-4

2019. New achievements in the synthesis of pyrrolo[1,2-a]quinoxalines. Chemistry of Heterocyclic Compounds, 55(7).
DOI: 10.1007/s10593-019-02501-w

2017. 2-(Azolyl)anilines: methods of synthesis, cyclocondensations, and biological properties. Chemistry of Heterocyclic Compounds, 53(3).
DOI: 10.1007/s10593-017-2051-7