2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine
[CAS# 1197953-49-3]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: 2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine
• Molecular Formula: C₁₂H₁₂Cl₂N₃OP
• Molecular Weight: 316.12
• CAS Registry Number: 1197953-49-3
• SMILES: CP(=O)(C)C1=CC=CC=C1NC2=NC(=NC=C2Cl)Cl

Properties

• Solubility: Very slightly soluble (0.47 g/L) (25 °C), Calc.^*
• Density: 1.41±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.597, Calc.^*
• Boiling Point: 527.5±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 272.8±30.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Discovery and Applications

2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine is a synthesized organic compound developed through targeted chemical research aimed at creating new molecules with potential pharmaceutical and agrochemical applications. This compound was discovered in the context of exploring pyrimidine derivatives, which are known for their biological activity, and integrating a dimethylphosphinyl group to enhance chemical properties. The synthesis involved multi-step organic reactions, including chlorination and phosphinylation processes, to introduce the desired functional groups. The discovery of this compound represents a significant advancement in the development of biologically active molecules with enhanced efficacy and stability.

The compound's structure, featuring both pyrimidine and phosphinyl groups, makes it a potential candidate for anticancer drug development. Pyrimidine derivatives are often key components in chemotherapeutic agents, and the addition of the dimethylphosphinyl group can enhance their ability to inhibit cancer cell proliferation. Research may focus on its efficacy against various cancer types and its mechanism of action at the molecular level.

This compound could be explored for anti-inflammatory properties, as similar pyrimidine derivatives have shown potential in modulating inflammatory pathways. Its structure might help in designing drugs that target specific enzymes or receptors involved in inflammatory responses.

In agrochemical applications, 2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine can be used to develop new herbicides. The chlorinated pyrimidine structure is effective in disrupting plant growth, and the phosphinyl group enhances its stability and activity. This makes it useful for controlling weeds in various crops, potentially increasing agricultural productivity.

The compound may also serve as a base for creating fungicides and pesticides. Its ability to interfere with biological processes in fungi and pests can protect crops from infections and infestations, contributing to sustainable agricultural practices.

The compound can act as an intermediate in the synthesis of more complex organic molecules. Its reactivity allows it to participate in further chemical modifications, enabling the creation of a wide range of derivatives for various applications.

In organic synthesis, the dimethylphosphinyl group can function as a ligand in catalysis, facilitating various chemical reactions. This property can be exploited to develop catalysts for industrial processes, enhancing efficiency and selectivity.

The incorporation of 2,5-Dichloro-N-[2-(dimethylphosphinyl)phenyl]-4-pyrimidinamine into polymer synthesis can yield materials with unique properties. The phosphinyl group can improve thermal stability and flame retardancy, making these materials suitable for high-performance applications in electronics, automotive, and aerospace industries.

The compound's stability and reactivity can be utilized in developing durable coatings and adhesives, providing enhanced performance in various environmental conditions.

References

2017. Brigatinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0179