16097-60-2 | 2-AMINO-4-CHLORO-6-TRIFLUOROMETHYL-PYRIMIDINE

CAS:16097-60-2 | 2-AMINO-4-CHLORO-6-TRIFLUOROMETHYL-PYRIMIDINE,Description

The compound 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine is a derivative of the pyrimidine family, which is a class of heterocyclic aromatic organic compounds. Pyrimidines are important in various biological processes as they are a component of nucleotides in DNA and RNA. The specific substitution pattern of the compound suggests potential for unique interactions and reactivity due to the presence of amino, chloro, and trifluoromethyl groups.

Synthesis Analysis

The synthesis of pyrimidine derivatives can be achieved through various methods. For instance, the regioselective synthesis of 4-amino-2,8-dichloropyrido[3,2-d]pyrimidine derivatives involves S(N)Ar and metal-catalyzed cross-coupling reactions, demonstrating the versatility of pyrimidine chemistry. Another approach is the one-step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines via a three-component condensation process. These methods highlight the synthetic accessibility of substituted pyrimidines, which could be adapted for the synthesis of 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine.

Molecular Structure Analysis

The molecular structure of pyrimidine derivatives is characterized by a planar six-membered ring with partial double-bond character in the C-C and C-N bonds. X-ray crystallography studies have revealed the planarity and bond characteristics of similar compounds, such as 2-amino-4-methyl-6-chloropyrimidine. The presence of substituents like chloro and trifluoromethyl groups would influence the electronic distribution and steric interactions within the molecule.

Chemical Reactions Analysis

Pyrimidine derivatives undergo various chemical reactions, including hydrogen bonding, which is crucial for molecular recognition processes. For example, the formation of unclassical hydrogen bonds C-H⋅⋅⋅O and C-H⋅⋅⋅N has been observed in the crystals of certain pyrimidine derivatives. The reactivity of the amino group in pyrimidine compounds allows for further functionalization, as seen in the acylation reactions with chlorocarboxylic acid chlorides.

Physical and Chemical Properties Analysis

The physical and optical properties of pyrimidine derivatives can be tailored by substituents. Compounds such as 2-amino-4-aryl-6-(9,9′-spirobifluoren-2-yl)pyrimidines exhibit good blue light emissions and excellent thermal stabilities, indicating the potential for material science applications. The introduction of a trifluoromethyl group in 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine would likely affect the compound's lipophilicity, volatility, and chemical stability, making it an interesting candidate for further study.

Scientific Research Applications

• Pyrimidines in Molecular Recognition Processes : Pyrimidines, including derivatives of 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine, play a crucial role in molecular recognition processes involving hydrogen bonding, which is vital in biology and medicine. This is evidenced by the analysis of crystallization of 4-amino-5-chloro-2,6-dimethylpyrimidine and its interaction with acids, demonstrating the importance of tautomerism and hydrogen bonding in molecular recognition (Rajam et al., 2017).
• Hydrogen-Bonded Structures : The structural analysis of 2-amino-4-chloro-5-formyl-6-[methyl(2-methylphenyl)amino]pyrimidine and its analogs shows how these compounds form hydrogen-bonded sheets, which is significant for understanding the isostructural nature of these compounds and their potential applications in materials science (Trilleras et al., 2009).
• Potential Antiallergic Activity : Compounds derived from 4-chloro-2-(4-pyridinyl)pyrimidines, related to 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine, have shown potential antiallergic activity as indicated by rat passive cutaneous anaphylaxis screening. This highlights the therapeutic potential of these compounds in treating allergies (Lesher et al., 1982).
• Degradation in Soil : A study on the degradation and persistence of 2-amino-4-chloro-6-methyl pyrimidine, a related compound, in subtropical soil, found that it degrades over time, fitting well to first-order kinetics. This is relevant for its use in increasing the efficiency of nitrogenous fertilizers in agriculture (Srivastava et al., 2016).
• Anti-Inflammatory and Antimicrobial Activity : Derivatives of 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine have been synthesized and evaluated for their antibacterial, antifungal, and anti-inflammatory activities. This demonstrates the potential pharmaceutical applications of these compounds (Dongarwar et al., 2011).
• Use in Synthesis of Functionalised Pyrimidine Systems : 5-Chloro-2,4,6-trifluoropyrimidine, a close relative of 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine, is assessed for its use as a core scaffold in synthesizing functionalized pyrimidine systems, demonstrating its potential in synthetic organic chemistry (Parks et al., 2008).

Safety And Hazards

The compound is considered hazardous. It has the GHS07 pictogram and the signal word is “Warning”. The hazard statements are H302-H315-H319-H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. The precautionary statements are P261-P305+P351+P338, advising to avoid breathing dust/fume/gas/mist/vapors/spray, and if in eyes, rinse cautiously with water for several minutes.

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