2-Hydroxy-6-methoxypyridine
[CAS# 22385-36-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Hydroxypyridine
• Name: 2-Hydroxy-6-methoxypyridine
• Synonyms: 6-methoxy-1H-pyridin-2-one
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.12
• CAS Registry Number: 22385-36-0
• EC Number: 961-388-3
• SMILES: COC1=CC=CC(=O)N1

Properties

• Solubility: 6.414e+005 mg/L (25 °C water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.539, Calc.^*
• Melting point: 84.42 °C
• Boiling Point: 309.3±22.0 °C (760 mmHg), Calc.^*, 291.59 °C
• Flash Point: 140.9±22.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

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.	2A	H319

Discovery and Applications

2-Hydroxy-6-methoxypyridine is an organic compound with the chemical formula C7H9NO2. It is a pyridine derivative characterized by the presence of a hydroxyl group (-OH) and a methoxy group (-OCH3) attached to the pyridine ring. The compound has gained attention in various fields due to its unique properties and diverse applications. The discovery of 2-hydroxy-6-methoxypyridine can be attributed to the systematic exploration of pyridine derivatives in organic chemistry during the late 19th and early 20th centuries, where researchers investigated their potential biological and chemical properties.

The synthesis of 2-hydroxy-6-methoxypyridine typically involves the methylation of 2-hydroxypyridine using methanol in the presence of a catalyst. Various synthetic routes have been developed, including methods that utilize pyridine and its derivatives as starting materials. The resulting product possesses unique chemical characteristics, making it suitable for a range of applications.

One of the primary applications of 2-hydroxy-6-methoxypyridine is in the field of agrochemicals. It is used as an intermediate in the synthesis of various herbicides and pesticides. The compound’s ability to interact with plant physiological processes has led to its incorporation into formulations aimed at enhancing crop protection and yield. Research has demonstrated that 2-hydroxy-6-methoxypyridine exhibits herbicidal activity, making it a valuable component in the development of effective agricultural chemicals.

In addition to its agricultural applications, 2-hydroxy-6-methoxypyridine is also explored in the pharmaceutical industry. The compound serves as a building block for the synthesis of various bioactive molecules, including pharmaceuticals and medicinal compounds. Its structural features allow it to interact with biological systems, making it a candidate for further research in drug development. Studies have indicated that derivatives of 2-hydroxy-6-methoxypyridine possess antimicrobial and anti-inflammatory properties, which are of great interest in therapeutic applications.

Furthermore, 2-hydroxy-6-methoxypyridine finds utility in the development of materials, particularly in the synthesis of polymers and resins. Its functional groups can participate in various chemical reactions, allowing for the creation of new materials with tailored properties. The incorporation of this compound into polymer formulations can enhance their thermal stability, mechanical strength, and chemical resistance, making them suitable for a wide range of industrial applications.

Despite its numerous beneficial applications, safety considerations regarding 2-hydroxy-6-methoxypyridine are essential. Regulatory agencies monitor its use in agrochemical and pharmaceutical formulations to ensure that it meets safety standards for consumer and environmental health. Manufacturers are required to adhere to guidelines that minimize potential risks associated with the compound's application.

In conclusion, 2-hydroxy-6-methoxypyridine is a versatile chemical compound with significant applications in agrochemicals, pharmaceuticals, and materials science. Its discovery and subsequent development have contributed to advancements in these fields, emphasizing the importance of ongoing research to explore its full potential and enhance its utility in various applications.

References

2022. Bare Magnetite-Promoted Oxidative Hydroxylation of Arylboronic Acids and Subsequent Conversion into Phenolic Compounds. *Synlett*, 33(10).
DOI: 10.1055/s-0040-1719926

1990. Electron and Proton Transfer Reactions. *Quantum Chemistry of Organic Compounds*.
DOI: 10.1007/978-3-642-75679-5_9