2,5-Dimethoxytetrahydrofuran
[CAS# 696-59-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 2,5-Dimethoxytetrahydrofuran
• Synonyms: Tetrahydro-2,5-dimethoxyfuran
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• CAS Registry Number: 696-59-3
• EC Number: 211-797-1
• SMILES: COC1CCC(O1)OC

Properties

• Water solubility: 350 g/L (20 °C)
• Density: 1.0±0.1 g/cm³, Calc.^*, 1.022 g/mL (20 °C) (Expl.)
• Melting point: -45 °C (Expl.)
• Index of Refraction: 1.423, Calc.^*, 1.418 (Expl.)
• Boiling Point: 145.7±0.0 °C (760 mmHg), Calc.^*, 145-147 °C (Expl.)
• Flash Point: 35.0±0.0 °C, Calc.^*, 35 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H315-H317-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P272-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1993

Discovery and Applications

2,5-Dimethoxytetrahydrofuran (DMTHF) is a cyclic ether compound that has garnered attention for its unique structure and versatile applications. As a derivative of tetrahydrofuran (THF), DMTHF features two methoxy groups attached to the 2 and 5 positions of the tetrahydrofuran ring, making it a significant modification with improved chemical properties. Its discovery can be traced back to the growing interest in developing solvents and reagents with specialized characteristics, particularly in the fields of organic synthesis and material science.

The chemical structure of 2,5-dimethoxytetrahydrofuran consists of a five-membered heterocyclic ring with four carbon atoms and one oxygen atom, similar to tetrahydrofuran, but with additional methoxy groups (–OCH3) at the 2 and 5 positions. These methoxy groups enhance the solubility and stability of the compound in various solvents, offering greater flexibility in its application across a range of chemical processes. Furthermore, the presence of the methoxy groups affects the polarity of the compound, which can make it useful as both a solvent and a reactant in specific synthetic routes.

One of the key applications of 2,5-dimethoxytetrahydrofuran is in organic synthesis, where it serves as a valuable solvent for a variety of chemical reactions. Its high solubility in both polar and nonpolar solvents makes it an ideal medium for reactions that require a stable and versatile environment. DMTHF is commonly used in reactions involving organometallic compounds, such as the Grignard reaction, and in the synthesis of pharmaceuticals and fine chemicals. Its stability and relatively low volatility make it suitable for use under controlled conditions, ensuring that reactions proceed efficiently without the risk of degradation or evaporation.

In addition to its role as a solvent, 2,5-dimethoxytetrahydrofuran is employed in polymer chemistry. It is used as a monomer or co-monomer in the production of various polymer materials, where its methoxy groups can influence the polymerization process and enhance the properties of the resulting material. DMTHF is often incorporated into copolymers and other advanced materials to provide increased flexibility, solubility, and processability, which are crucial for applications in coatings, adhesives, and films.

Another area where DMTHF finds significant utility is in electrochemical applications. Due to its ability to dissolve a wide range of salts and organic compounds, it is used as a solvent in the preparation of electrolyte solutions for batteries and capacitors. The compound’s stability and high dielectric constant contribute to its effectiveness in these systems, helping to improve the performance and longevity of electrochemical devices.

Furthermore, 2,5-dimethoxytetrahydrofuran is a potential candidate for use in the development of new materials for environmental applications. Its ability to interact with various types of organic and inorganic compounds has led to research into its role in environmental remediation processes, such as the removal of pollutants or the degradation of harmful substances.

While 2,5-dimethoxytetrahydrofuran is primarily recognized for its role in synthetic chemistry and materials science, its discovery has paved the way for further exploration of its potential applications. As research into its properties and capabilities continues to expand, it is likely that new uses for this compound will emerge, particularly in fields that require the precise control of chemical reactions and the development of advanced materials.

In conclusion, 2,5-dimethoxytetrahydrofuran is a versatile chemical compound with a wide range of applications across various industries, from organic synthesis and polymer chemistry to electrochemical systems and environmental remediation. Its discovery and ongoing development highlight its importance as a reagent and solvent in advanced chemical processes, demonstrating its value in both academic research and industrial applications.

References

2021. Recent Advancements in Pyrrole Synthesis. Synthesis, 53(10).
DOI: 10.1055/s-0040-1706713

2018. Solvent Free Synthesis of N-Substituted Pyrrole Derivatives Catalyzed by Silica Sulfuric Acid. Russian Journal of General Chemistry, 88(12).
DOI: 10.1134/s1070363218120332

2020. Benzannulation of Thiophenes with 2,5-Dimethoxytetrahydrofuran. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-110-01819