4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile
[CAS# 189956-45-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Hydroxypyrimidine
• Name: 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile
• Synonyms: 4-[(1,4-Dihydro-4-oxo-2-pyrimidinyl)amino]benzonitrile
• Molecular Formula: C₁₁H₈N₄O
• Molecular Weight: 212.21
• CAS Registry Number: 189956-45-4
• EC Number: 606-195-4
• SMILES: C1=CC(=CC=C1C#N)NC2=NC=CC(=O)N2

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.677, Calc.^*
• Boiling Point: 482.3±51.0 ºC (760 mmHg), Calc.^*
• Flash Point: 245.5±30.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H318
• Precautionary Statements: P264+P265-P280-P305+P354+P338-P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile is a compound that has attracted significant interest in the field of organic chemistry due to its unique structural features and potential applications in various industries, particularly in the areas of pharmaceuticals and agrochemicals. This chemical consists of a benzonitrile group substituted with an amino group attached to a pyrimidine ring that also contains a hydroxyl group at the 4-position. The combination of these functional groups gives the molecule distinct reactivity, making it a valuable intermediate for further chemical modifications.

The discovery of 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile arose from efforts to develop compounds with potential biological activity. Pyrimidine-based compounds are well-known for their utility in medicinal chemistry, with several pyrimidine derivatives being incorporated into drugs targeting a variety of diseases, including cancer, infections, and inflammatory conditions. The incorporation of a hydroxyl group on the pyrimidine ring adds an additional site for potential chemical interactions, while the benzonitrile moiety provides the compound with unique electronic properties that can influence its behavior in biological systems.

One of the primary applications of 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile is as a building block in the synthesis of more complex molecules. The pyrimidine and benzonitrile functionalities make it an attractive intermediate in the design of compounds with potential therapeutic applications. For instance, this substance can be utilized in the development of kinase inhibitors, which are valuable in the treatment of cancers and other diseases where abnormal kinase activity plays a role. The hydroxyl group on the pyrimidine ring may also provide opportunities for hydrogen bonding with biological targets, improving the compound's binding affinity and specificity.

In addition to its use in drug discovery, 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile has applications in the agrochemical industry. The compound's ability to interact with enzymes and receptors makes it a potential candidate for developing new agrochemicals, such as herbicides or fungicides. Pyrimidine-based molecules are known to have pesticidal activity, and derivatives of 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile may exhibit activity against pests or pathogens, providing an alternative to traditional pesticides.

The compound’s utility in organic synthesis also extends to the creation of materials with specialized properties. The benzonitrile core offers an opportunity for designing materials that can undergo specific chemical reactions or interact with certain environmental factors, such as light or heat. These properties can be exploited in the creation of novel sensors or materials with advanced functionalities in fields like optoelectronics or environmental monitoring.

Moreover, 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile can be modified to create new derivatives with enhanced biological or chemical properties. Researchers can use this compound as a starting point for the synthesis of compounds that may show better bioactivity or higher selectivity toward particular biological targets. Its chemical structure also makes it a useful reagent in various reactions, including nucleophilic substitutions and condensation reactions, which are essential in organic synthesis.

In summary, 4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile is a valuable compound with a range of potential applications in drug discovery, agrochemicals, and materials science. Its unique structural characteristics, including the presence of a pyrimidine ring with a hydroxyl group and a benzonitrile moiety, make it an attractive candidate for developing new therapeutic agents and chemical materials. Ongoing research into its synthesis and functionalization continues to reveal its versatility in various fields.

References

2014. Structural modification of diarylpyrimidine derivatives as HIV-1 reverse transcriptase inhibitors. Medicinal Chemistry Research, 23(12). DOI: 10.1007/s00044-014-1119-5