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Cyclopentyl methyl ether

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Cyclopentyl methyl ether 
Cyclopentyl methyl ether
Names
IUPAC name
methoxycyclopentane
Other names
CPME
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.104.006 Edit this at Wikidata
  • InChI=1S/C6H12O/c1-7-6-4-2-3-5-6/h6H,2-5H2,1H3
    Key: SKTCDJAMAYNROS-UHFFFAOYSA-N
  • COC1CCCC1
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance colourless clear liquid
Density 0.86 g/cm3
Melting point −140 °C (−220 °F; 133 K)
Boiling point 106 °C (223 °F; 379 K)
0,011 g/g in Water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant (Xi)
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point −1 °C (30 °F; 272 K)
Safety data sheet (SDS) MSDS [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclopentyl methyl ether(CPME), also known as methoxy cyclopentane, it is hydrophobic ether solvent. A high boiling point (106 °C) and preferable characteristics such as low formation of peroxides, relative stability under acidic and basic conditions, formation of azeotropes with water coupled with a narrow explosion range render CPME an alternative to other ethereal solvents such as tetrahydrofuran (THF), 2-methyl tetrahydrofuran (2-MeTHF), dioxane (carcinogenic), and 1,2-dimethoxyethane (DME).[1]


Synthesis

The synthesis of this compound can be done in two different ways:


(1) by methylation of the cyclopentanol.


(2) by the addition of methanol to the cyclopentene. This second method is better from the point of view of sustainable chemistry since it does not produce by-products.



Applications

Cyclopentyl methyl ether is used in organic synthesis, mainly as a solvent. However it is also useful in extractions, polymerizations, crystallization and surface coatings.

Some examples of reactions where it acts as a solvent are:

  • Reactions involving alkali agents: nucleophilic substitutions of heteroatoms (alcohols and amines)
  • Lewis acids-mediated reactions: Beckmann Reaction, Friedel-Crafts etc.
  • Reactions using Organometallic or basic agents: Claisen condensation, formation of enolates or Grignard reaction.
  • Reduction and oxidation.
  • Reactions with transition metal catalysts.

References

  1. ^ "Cyclopentyl Methyl Ether as a New and Alternative Process Solvent". Org. Process Res. Dev., 2007, 11 (2), pp 251–258,: 4671. February 24, 2007.{{cite journal}}: CS1 maint: extra punctuation (link)
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