Cas no 102015-02-1 (2-tert-butyl-6-hydroxypyridine-4-carboxylic acid)

2-tert-Butyl-6-hydroxypyridine-4-carboxylic acid is a substituted pyridine derivative with a tert-butyl group at the 2-position and a hydroxyl group at the 6-position, along with a carboxylic acid functionality at the 4-position. This compound is of interest in synthetic chemistry due to its versatile reactivity, particularly as a building block for pharmaceuticals, agrochemicals, and coordination chemistry. The tert-butyl group enhances steric hindrance, potentially improving selectivity in reactions, while the hydroxyl and carboxylic acid groups offer sites for further functionalization or metal chelation. Its structural features make it useful in designing ligands or intermediates with tailored properties for catalytic or biological applications.
2-tert-butyl-6-hydroxypyridine-4-carboxylic acid structure
102015-02-1 structure
Product Name:2-tert-butyl-6-hydroxypyridine-4-carboxylic acid
CAS No:102015-02-1
MF:C10H13NO3
MW:195.215122938156
MDL:MFCD20642230
CID:2865754
Update Time:2025-06-12

2-tert-butyl-6-hydroxypyridine-4-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 6-tert-Butyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid
    • 6-tert-butyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid
    • 6-(tert-butyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid
    • BBL033427
    • STL309360
    • STL373280
    • 2-(tert-Butyl)-6-hydroxyisonicotinic acid
    • 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid
    • 2-tert-butyl-6-oxo-1H-pyridine-4-carboxylic acid
    • MDL: MFCD20642230
    • Inchi: 1S/C10H13NO3/c1-10(2,3)7-4-6(9(13)14)5-8(12)11-7/h4-5H,1-3H3,(H,11,12)(H,13,14)
    • InChI Key: KDJDPVXVRFKEDR-UHFFFAOYSA-N
    • SMILES: O=C1C=C(C(=O)O)C=C(C(C)(C)C)N1

Computed Properties

  • Exact Mass: 195.089543g/mol
  • Monoisotopic Mass: 195.089543g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 345
  • 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
  • XLogP3: 1.1
  • Topological Polar Surface Area: 66.4
  • Molecular Weight: 195.21g/mol

Experimental Properties

  • Color/Form: NA
  • Density: 1.2±0.1 g/cm3
  • Boiling Point: 367.5±42.0 °C at 760 mmHg
  • Flash Point: 178.0±22.3 °C

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Additional information on 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid

Introduction to 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid (CAS No. 102015-02-1)

2-tert-butyl-6-hydroxypyridine-4-carboxylic acid, identified by the Chemical Abstracts Service (CAS) number 102015-02-1, is a significant compound in the realm of pharmaceutical and chemical research. This compound belongs to the pyridine family, a heterocyclic aromatic organic compound characterized by a nitrogen atom within its six-membered ring structure. The presence of both hydroxyl and carboxylic acid functional groups, along with a tert-butyl substituent, imparts unique chemical properties that make it a valuable intermediate in synthetic chemistry and drug development.

The structure of 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid features a pyridine core with a hydroxyl group at the 6-position and a carboxylic acid group at the 4-position. The tert-butyl group, attached at the 2-position, enhances the steric hindrance around the ring, influencing its reactivity and interaction with biological targets. This structural arrangement not only makes it an interesting subject for mechanistic studies but also opens up possibilities for designing novel pharmacophores.

In recent years, there has been growing interest in pyridine derivatives due to their broad spectrum of biological activities. The hydroxyl and carboxylic acid functionalities in 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid provide multiple sites for chemical modification, enabling the synthesis of complex molecules with tailored properties. These modifications are crucial for developing drugs that can interact selectively with biological receptors or enzymes.

One of the most compelling aspects of this compound is its potential application in drug discovery and development. Pyridine derivatives are well-known for their role as key components in many therapeutic agents, including antiviral, antibacterial, and anticancer drugs. The unique combination of functional groups in 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid makes it a versatile building block for constructing novel molecules with enhanced pharmacological profiles.

Recent studies have highlighted the importance of substituted pyridines in medicinal chemistry. For instance, researchers have demonstrated that incorporating bulky groups like tert-butyl can improve the solubility and metabolic stability of drug candidates. This observation is particularly relevant for 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid, which may serve as a precursor for developing more effective therapeutic agents.

The synthesis of 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid involves multi-step organic reactions that require careful optimization to achieve high yields and purity. Common synthetic routes include functional group transformations such as hydroxylation, carboxylation, and alkylation. Advanced techniques like catalytic hydrogenation and palladium-catalyzed cross-coupling reactions are often employed to construct the desired pyridine framework efficiently.

Once synthesized, this compound can be further modified to explore its potential as a pharmaceutical intermediate. For example, the carboxylic acid group can be esterified or amidated to enhance bioavailability or target specific biological pathways. Similarly, the hydroxyl group can be used to form ether or thioether linkages, expanding the structural diversity of derived compounds.

In addition to its pharmaceutical applications, 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid has shown promise in material science and catalysis. Its ability to act as a ligand in transition metal complexes has been explored for designing efficient catalysts for various organic transformations. The steric bulk provided by the tert-butyl group can influence the electronic properties of these complexes, making them more selective or active depending on the application.

The biological activity of 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid has also been investigated in detail. Preliminary studies suggest that this compound may exhibit interactions with certain enzymes or receptors due to its structural features. These interactions could be leveraged to develop new treatments for diseases where such targets are involved. Further research is needed to fully elucidate its pharmacological effects and potential therapeutic uses.

One notable aspect of this compound is its stability under various conditions, which makes it suitable for long-term storage and transportation without significant degradation. This stability is attributed to the robust nature of its molecular structure and the absence of labile functional groups that are prone to hydrolysis or oxidation.

The analytical characterization of 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid is critical for ensuring its quality and purity before use in research or industrial applications. Techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC) are commonly employed to confirm its identity and assess its purity profile.

In conclusion, 2-tert-butyl-6-hydroxypyridine-4-carboxylic acid (CAS No. 102015-02-1) is a multifaceted compound with significant potential in pharmaceutical research and beyond. Its unique structural features make it an excellent candidate for synthesizing novel molecules with tailored biological activities. As research continues to uncover new applications for pyridine derivatives, this compound is likely to play an increasingly important role in drug discovery and development efforts worldwide.

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