Cas no 72790-17-1 (2-propylpyrimidine-5-carboxylic acid)

2-Propylpyrimidine-5-carboxylic acid is a pyrimidine derivative with a carboxyl functional group at the 5-position and a propyl substituent at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. Its structural features enable further functionalization, making it valuable for constructing heterocyclic frameworks. The carboxylic acid moiety allows for easy derivatization into esters, amides, or other derivatives, enhancing its utility in medicinal chemistry. The propyl group contributes to lipophilicity, which can influence bioavailability in drug design. This compound is typically characterized by high purity and stability, ensuring reliable performance in synthetic applications.
2-propylpyrimidine-5-carboxylic acid structure
72790-17-1 structure
Product Name:2-propylpyrimidine-5-carboxylic acid
CAS No:72790-17-1
MF:C8H10N2O2
MW:166.177201747894
MDL:MFCD11519807
CID:550558
PubChem ID:14056314
Update Time:2025-06-07

2-propylpyrimidine-5-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 5-Pyrimidinecarboxylicacid, 2-propyl-
    • 2-ethyl-pyrimidine-5-carboxylic acid
    • 2-Ethyl-5-pyrimidinecarboxylic acid
    • 2-propyl-5-Pyrimidinecarboxylic acid
    • 2-propylpyrimidine-5-carboxylic acid
    • CS-0297281
    • C80031
    • AS-63283
    • FT-0748928
    • AKOS000284165
    • EN300-768308
    • SB56912
    • 72790-17-1
    • DA-18643
    • MDL: MFCD11519807
    • Inchi: 1S/C8H10N2O2/c1-2-3-7-9-4-6(5-10-7)8(11)12/h4-5H,2-3H2,1H3,(H,11,12)
    • InChI Key: CVQIPAUPMBPXFQ-UHFFFAOYSA-N
    • SMILES: OC(C1C=NC(CCC)=NC=1)=O

Computed Properties

  • Exact Mass: 166.0743
  • Monoisotopic Mass: 166.074227566g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 141
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 4
  • XLogP3: 0.6
  • Topological Polar Surface Area: 63.1?2

Experimental Properties

  • PSA: 63.08

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2-propylpyrimidine-5-carboxylic acid Related Literature

Additional information on 2-propylpyrimidine-5-carboxylic acid

Introduction to 2-propylpyrimidine-5-carboxylic acid (CAS No. 72790-17-1)

2-propylpyrimidine-5-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 72790-17-1, is a significant compound in the realm of organic chemistry and pharmaceutical research. This heterocyclic carboxylic acid derivative has garnered attention due to its structural versatility and potential applications in drug development, agrochemicals, and material science. The compound features a pyrimidine core substituted with a propyl group at the 2-position and a carboxylic acid functional group at the 5-position, making it a valuable intermediate for synthesizing more complex molecules.

The molecular structure of 2-propylpyrimidine-5-carboxylic acid contributes to its reactivity and utility in various chemical transformations. The pyrimidine ring, a six-membered aromatic heterocycle containing two nitrogen atoms, is a common motif in biologically active compounds. The presence of the propyl side chain enhances the compound's solubility and interaction with biological targets, while the carboxylic acid group provides opportunities for further functionalization, such as esterification or amidation. These features make it a promising candidate for medicinal chemistry applications.

In recent years, there has been growing interest in developing novel pyrimidine derivatives as pharmacological agents. Pyrimidine-based scaffolds are prevalent in therapeutic drugs due to their ability to mimic natural nucleobases and interact with biological macromolecules like enzymes and receptors. Among these derivatives, 2-propylpyrimidine-5-carboxylic acid has been explored for its potential role in inhibiting various enzymatic pathways associated with diseases such as cancer, inflammation, and infectious disorders. Its structural motif is reminiscent of several known bioactive molecules, suggesting that it may serve as a lead compound or intermediate in the synthesis of new drugs.

One of the most compelling aspects of 2-propylpyrimidine-5-carboxylic acid is its role in the synthesis of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is often linked to cancer and other chronic diseases. Researchers have been actively searching for small-molecule inhibitors that can modulate kinase activity without significant off-target effects. The pyrimidine core of 2-propylpyrimidine-5-carboxylic acid provides a scaffold that can be modified to target specific kinases. For instance, studies have shown that derivatives of this compound can interact with the ATP-binding pockets of kinases, thereby inhibiting their activity. This has led to investigations into its potential as an anti-cancer agent.

Furthermore, 2-propylpyrimidine-5-carboxylic acid has been investigated for its antimicrobial properties. The pyrimidine ring is known to exhibit broad-spectrum activity against bacteria, fungi, and viruses due to its ability to disrupt nucleic acid synthesis or cellular metabolism. The introduction of the propyl group and the carboxylic acid moiety may enhance these properties by improving cell membrane penetration or binding affinity. Preliminary studies have demonstrated that certain derivatives of this compound can inhibit the growth of pathogenic microorganisms, making it a candidate for developing new antimicrobial agents.

The agrochemical industry has also shown interest in 2-propylpyrimidine-5-carboxylic acid due to its potential as a precursor for herbicides and pesticides. Pyrimidine-based compounds are widely used in agriculture because they can selectively target weed or pest species without harming crops. By modifying the structure of 2-propylpyrimidine-5-carboxylic acid, chemists can develop novel agrochemicals that offer improved efficacy and environmental safety. For example, derivatives of this compound have been tested for their ability to inhibit plant growth regulators or disrupt metabolic pathways in pests.

The synthesis of 2-propylpyrimidine-5-carboxylic acid involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include condensation reactions between propylamine derivatives and barbituric acid or malonic esters under acidic conditions. Alternatively, palladium-catalyzed cross-coupling reactions can be employed to introduce the propyl group onto a pre-formed pyrimidine ring. Advances in catalytic methods have improved the efficiency and sustainability of these synthetic processes, making it more feasible to produce larger quantities of this compound for research and industrial applications.

In conclusion, 2-propylpyrimidine-5-carboxylic acid (CAS No. 72790-17-1) is a versatile compound with significant potential in pharmaceuticals, agrochemicals, and material science. Its unique structural features make it a valuable intermediate for synthesizing bioactive molecules, particularly kinase inhibitors and antimicrobial agents. Ongoing research continues to explore new derivatives and applications of this compound, highlighting its importance in modern chemical research. As our understanding of its properties grows, so too does its promise as a building block for innovative solutions across multiple industries.

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