Cyclopentyl methyl ether

Cyclopentyl methyl ether (CPME), also known as methoxycyclopentane, is hydrophobic ether solvent. A high boiling point of 106 °C (223 °F) 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-methyltetrahydrofuran (2-MeTHF), dioxane, and 1,2-dimethoxyethane (DME).[2]

Cyclopentyl methyl ether
Names
IUPAC name
Methoxycyclopentane
Other names
CPME
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.104.006
EC Number
  • 445-090-6
UNII
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance Colorless clear liquid
Density 0.8630 g/cm3 (20 °C) [1]
Melting point −140 °C (−220 °F; 133 K)
Boiling point 106 °C (223 °F; 379 K) [1]
0.011 g/g
Hazards
Safety data sheet MSDS
GHS pictograms
GHS Signal word Danger
H225, H302, H312, H315, H319
P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+312, P302+352, P303+361+353, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P370+378, P403+235, P501
NFPA 704 (fire diamond)
Flammability code 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. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point −1 °C (30 °F; 272 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 extraction, polymerization, crystallization and surface coating.

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

  • Reactions involving alkali agents: nucleophilic substitutions of heteroatoms (alcohols and amines) [3]
  • Lewis acids-mediated reactions: Beckmann Reaction, Friedel-Crafts Reaction etc.[4]
  • Reactions using Organometallic reagents or basic agents: Claisen condensation, formation of enolates or Grignard reaction.[5]
  • Reduction and oxidation.[6]
  • Reactions with transition metal catalysts.[7]
  • Reactions with azeotropical removal of water: acetalization, etc.[8]

References
  1. Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville (6 Nov 2019). "Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds". International Journal of Thermophysics. 40 (11): 102. Bibcode:2019IJT....40..102B. doi:10.1007/s10765-019-2570-9.
  2. Watanabe, Kiyoshi; Yamagiwa, Noriyuki; Torisawa, Yasuhiro (February 24, 2007). "Cyclopentyl Methyl Ether as a New and Alternative Process Solvent". Org. Process Res. Dev. 11 (2): 251–258. doi:10.1021/op0680136.
  3. Ether compounds and polymerizable compounds and manufacturing methods. By: Kiriki, Satoshi.Aug 3, 2015.JP 2015140302
  4. Torisawa, Yasuhiro (15 January 2007). "Conversion of indanone oximes into isocarbostyrils". Bioorganic & Medicinal Chemistry Letters. 17 (2): 453–455. doi:10.1016/j.bmcl.2006.10.022. PMID 17064893.
  5. Okabayashi, Tomohito; Iida, Akira; Takai, Kenta; Misaki, Tomonori; Tanabe, Yoo (September 18, 2007). "Practical and Robust Method for Regio- and Stereoselective Preparation of (E)-Ketene tert-Butyl TMS Acetals and β-Ketoester-derived tert-Butyl (1Z,3E)-1,3-Bis(TMS)dienol Ethers". The Journal of Organic Chemistry. 72 (21): 8142–8145. doi:10.1021/jo701456t. PMID 17877405.
  6. Shimada, Toyoshi; Suda, Masahiko; Nagano, Toyohiro; Kakiuchi, Kiyomi (October 22, 2005). "Facile Preparation of a New BINAP-Based Building Block, 5,5'-DiiodoBINAP, and Its Synthetic Application". The Journal of Organic Chemistry. 70 (24): 10178–10181. doi:10.1021/jo0517186. PMID 16292868.
  7. Molander, Gary A.; Elia, Maxwell D. (November 3, 2006). "Suzuki−Miyaura Cross-Coupling Reactions of Benzyl Halides with Potassium Aryltrifluoroborates". The Journal of Organic Chemistry. 71 (24): 9198–9202. doi:10.1021/jo061699f. PMC 2515367. PMID 17109547.
  8. Azzena, Ugo; Carraro, Massimo; Mamuye, Ashenafi Damtew; Murgia, Irene; Pisano, Luisa; Zedde, Giuseppe (17 April 2015). "Cyclopentyl methyl ether – NH4X: a novel solvent/ catalyst system for low impact acetalization reactions". Green Chemistry. 17 (6): 3281–3284. doi:10.1039/c5gc00465a.
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