4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile
[CAS# 329187-59-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Chloropyridine
• Name: 4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile
• Synonyms: 2-(4-Cyanophenylamino)-4,6-dichloropyrimidine
• Molecular Formula: C₁₁H₆Cl₂N₄
• Molecular Weight: 265.10
• CAS Registry Number: 329187-59-9
• SMILES: C1=CC(=CC=C1C#N)NC2=NC(=CC(=N2)Cl)Cl

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.66, Calc.^*
• Boiling Point: 468.9±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 237.4±31.5 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile is a chemical compound used primarily in the field of medicinal chemistry, particularly as a potential precursor in the development of pharmaceutical agents. This compound consists of a benzonitrile group (a benzene ring attached to a nitrile group, -C≡N) substituted at the 4-position with a 4,6-dichloro-2-pyrimidinylamino group, which provides its key functional and structural properties.

The discovery of 4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile is tied to the exploration of pyrimidine derivatives in drug design, particularly in the development of inhibitors targeting various enzymes and receptors involved in disease processes. Pyrimidine-containing compounds are known for their biological activity, and derivatives like this one have been of interest for their potential in targeting specific molecular pathways, including those involved in cancer, inflammation, and microbial infections.

One of the most notable applications of 4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile is its use as an intermediate or precursor in the synthesis of other bioactive molecules, particularly those aimed at modulating enzymatic activity. Compounds with similar structures have been studied for their ability to inhibit protein kinases, which are crucial in regulating various cellular functions and are implicated in the development of various diseases, including cancer and autoimmune disorders. The pyrimidine ring in the compound plays a significant role in these interactions, often acting as a key binding moiety for the active site of target enzymes.

In addition to its role in drug development, 4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile has been explored for its potential use in agricultural chemistry. Pyrimidine derivatives are known to possess antimicrobial properties, and similar compounds have been tested for their efficacy as herbicides or fungicides. The substitution pattern on the pyrimidine ring, particularly the presence of the dichloro substituents, can influence the compound's biological activity and its ability to inhibit the growth of certain pests or pathogens.

This compound is also utilized in the synthesis of other complex organic molecules through various chemical reactions, such as nucleophilic substitution or condensation reactions, where it can act as a building block in the creation of more complex heterocyclic compounds. These reactions are important in the production of various fine chemicals and specialty materials used in the pharmaceutical and agrochemical industries.

In summary, 4-[(4,6-Dichloro-2-pyrimidinyl)amino]benzonitrile is an important chemical intermediate in the synthesis of bioactive compounds, particularly those targeting protein kinases or other enzymes involved in disease processes. Its structural features, including the pyrimidine and nitrile groups, contribute to its reactivity and utility in medicinal chemistry. The compound has applications in drug discovery, particularly in the development of kinase inhibitors, as well as potential uses in agricultural chemistry for pest control.