2,5-Dimethoxypyridine
[CAS# 867267-24-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 2,5-Dimethoxypyridine
• Molecular Formula: C₇H₉NO₂
• Molecular Weight: 139.15
• CAS Registry Number: 867267-24-1
• EC Number: 800-641-3
• SMILES: COC1=CN=C(C=C1)OC

Properties

• Solubility: Sparingly soluble (17 g/L) (25 °C), Calc.^*
• Density: 1.064±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 203.5±20.0 °C (760 Torr), Calc.^*
• Flash point: 73.2±12.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2,5-Dimethoxypyridine is a versatile chemical compound that has gained prominence in organic synthesis due to its unique structural features and reactivity. This compound is an aromatic heterocycle featuring a pyridine ring with two methoxy groups attached at the 2 and 5 positions, which significantly influences its chemical behavior and applications.

The discovery of 2,5-Dimethoxypyridine can be traced back to the early 20th century when researchers began exploring the chemical properties of substituted pyridines. The introduction of methoxy groups at specific positions on the pyridine ring was found to enhance the reactivity of the molecule, leading to its use as an important building block in various chemical transformations.

One of the primary applications of 2,5-Dimethoxypyridine is in the field of organic synthesis, where it serves as a valuable intermediate in the preparation of complex molecules. The compound's methoxy substituents make it an excellent candidate for nucleophilic substitution reactions, allowing chemists to modify the pyridine ring to introduce various functional groups. This versatility makes 2,5-Dimethoxypyridine an essential tool for the synthesis of diverse organic compounds, including pharmaceuticals and agrochemicals.

In medicinal chemistry, 2,5-Dimethoxypyridine is used as a precursor for the synthesis of biologically active molecules. Its ability to participate in various chemical reactions enables the creation of compounds with potential therapeutic properties. For instance, the methoxy groups can be utilized to modify the electronic properties of the pyridine ring, influencing the molecule's interaction with biological targets and enhancing its pharmacological activity.

Another significant application of 2,5-Dimethoxypyridine is in the development of agrochemicals. The compound is employed in the synthesis of pesticides and herbicides, where its ability to form stable derivatives plays a crucial role. The methoxy groups contribute to the compound's solubility and stability, which are essential characteristics for the efficacy of agrochemical products.

Additionally, 2,5-Dimethoxypyridine is used in the preparation of fluorescent dyes and indicators. The methoxy substituents on the pyridine ring can influence the optical properties of the molecule, making it suitable for applications in fluorescence spectroscopy and other analytical techniques. These dyes and indicators are valuable in various scientific fields, including biology and materials science, where they are used to monitor chemical reactions and detect specific analytes.

Overall, 2,5-Dimethoxypyridine is a valuable compound in organic synthesis due to its reactivity and versatility. Its applications span across medicinal chemistry, agrochemicals, and analytical chemistry, making it an important tool for researchers and industrial chemists involved in the development of new molecules and materials.

References

2005. A Regioselective Route to 5- and 6-Azaindoles. Synlett, 2005(11).
DOI: 10.1055/s-2005-871946