Cyclopentyl methyl ether
[CAS# 5614-37-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: Cyclopentyl methyl ether
• Synonyms: methoxycyclopentane
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• CAS Registry Number: 5614-37-9
• EC Number: 611-360-9
• SMILES: COC1CCCC1

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*, 0.86 g/mL (Expl.)
• Melting point: -140 °C (Expl.)
• Boiling point: 105.3±8.0 °C 760 mmHg (Calc.)^*, 106 °C (Expl.)
• Flash point: 6.5±14.2 °C (Calc.)^*, -1 °C (Expl.)
• Index of refraction: 1.423 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H302-H312-H315-H319
• Safety Statements: P210-P233-P240-P241-P242-P243-P264-P264+P265-P270-P280-P301+P317-P302+P352-P303+P361+P353-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

• Transport Information: UN 3271

Discovery and Applications

Cyclopentyl methyl ether (CPME) is an organic solvent belonging to the class of alkyl ethers, with the chemical formula C₆H₁₂O. It consists of a cyclopentyl group bonded to a methyl ether moiety, forming a five-membered cycloalkyl ring attached through an oxygen atom to a methyl group. CPME has gained attention in recent years as an alternative solvent in organic synthesis due to its favorable physicochemical properties.

The discovery and development of cyclopentyl methyl ether as a solvent arose from the need for safer and more environmentally friendly solvents with good performance in various chemical reactions. CPME offers advantages such as low peroxide formation, relatively high boiling point (around 106–108°C), low water solubility, and chemical stability, which make it a practical solvent for many synthetic procedures.

CPME is widely used as a solvent in organic synthesis, including reactions such as Grignard additions, reductions, and various cross-coupling reactions. Its stability under acidic and basic conditions allows it to be employed in processes that may degrade more common ethers like tetrahydrofuran (THF). The low miscibility with water facilitates easier product separation and solvent recovery. Additionally, CPME’s relatively low volatility and favorable safety profile contribute to its adoption as a greener solvent alternative.

In industrial and laboratory settings, CPME serves as a replacement for more hazardous solvents such as dichloromethane and diethyl ether in certain applications. Its chemical inertness and compatibility with a wide range of reagents and catalysts enhance its utility. CPME is also favored for its reduced environmental impact, including lower toxicity and less contribution to volatile organic compound (VOC) emissions.

Analytical characterization of cyclopentyl methyl ether typically involves techniques such as gas chromatography (GC) for purity assessment and nuclear magnetic resonance (NMR) spectroscopy to confirm molecular structure. Infrared (IR) spectroscopy is used to identify characteristic ether functional group absorptions.

In summary, cyclopentyl methyl ether is a cycloalkyl ether solvent valued for its chemical stability, low peroxide formation, and environmental benefits. It is increasingly used in organic synthesis and industrial processes as a safer and more sustainable alternative to traditional ether solvents.

References

2024. Cyclopentyl Methyl Ether (CPME). Biorenewable Solvents for Organic Synthesis.
DOI: 10.1007/978-3-031-74346-7_3

2012. Ring-Expansion Reaction of Oximes with Aluminum Reductants. Molecules (Basel, Switzerland), 17(6).
DOI: 10.3390/molecules17067348

2011. Cyclopentyl Methyl Ether: An Alternative Solvent for Palladium-Catalyzed Direct Arylation of Heteroaromatics. ChemSusChem, 4(2).
DOI: 10.1002/cssc.201000405