2,4-Dihydroxypyridine
[CAS# 626-03-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Hydroxypyridine
• Name: 2,4-Dihydroxypyridine
• Synonyms: 2,4-Pyridinediol; 3-Deazauracil; 4-Hydroxy-2-pyridone
• Molecular Formula: C₅H₅NO₂
• Molecular Weight: 111.10
• CAS Registry Number: 626-03-9
• EC Number: 210-924-8
• SMILES: C1=CNC(=O)C=C1O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 272-276 °C (Expl.)
• Index of Refraction: 1.625, Calc.^*
• Boiling Point: 509.8±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 262.1±24.6 °C, Calc.^*

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,4-Dihydroxypyridine is an organic compound with the chemical formula C5H5NO2. It belongs to the class of heterocyclic compounds, specifically pyridine derivatives, and is characterized by the presence of two hydroxyl groups located at the 2 and 4 positions on the pyridine ring. This compound is often used as an intermediate in the synthesis of other organic compounds and has found applications in several areas of chemical and pharmaceutical research.

The discovery of 2,4-dihydroxypyridine is closely tied to the study of pyridine derivatives, which are significant in medicinal chemistry due to their diverse biological activities. Pyridine and its derivatives, including 2,4-dihydroxypyridine, have been explored for their potential therapeutic effects, including their role as enzyme inhibitors and their interaction with various biological targets. The compound itself has been found to possess certain antioxidant properties, which makes it of interest in studies related to oxidative stress and free radical scavenging.

In addition to its role in organic synthesis, 2,4-dihydroxypyridine has been examined for its use in the design of metal-chelating agents. The hydroxyl groups on the pyridine ring are capable of coordinating with metal ions, a feature that is useful in various chemical applications, including the formation of complexes with transition metals. These metal complexes can be used in catalysis or as part of coordination chemistry studies.

Furthermore, the compound has been explored in the synthesis of heterocyclic systems that exhibit biological activity, particularly as part of research into compounds with potential neuroprotective, anti-inflammatory, or anticancer properties. The presence of the hydroxyl groups in 2,4-dihydroxypyridine offers opportunities for functionalization, which can lead to the development of more complex molecules with enhanced bioactivity.

In conclusion, 2,4-dihydroxypyridine is a pyridine derivative with applications in organic synthesis and pharmaceutical research. Its role as a precursor for more complex molecules, as well as its potential biological activity and ability to form metal complexes, makes it a compound of interest in various areas of chemical research.

References

1965. Synthesen von Heterocyclen, 75. Mitt.: über 4-Hydroxy-pyridone. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften, 96(5).
DOI: 10.1007/bf00904285

2019. Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold. Molecular Diversity, 24(2).
DOI: 10.1007/s11030-019-09968-x

2023. One-pot Biginelli synthesis of novel series of 2-oxo/thioxo/imino-1,2,3,4-tetrahydropyrimidine based on 4-hydroxy-2-pyridone. Chemical Papers, 77(9).
DOI: 10.1007/s11696-023-02832-1