Cyclopentyl methyl ether

Cyclopentyl methyl ether
Names
Chemical structure of cyclopentyl methyl ether
Preferred IUPAC name Methoxycyclopentane
Other names CPME
Identifiers
CAS Number	5614-37-9^Y
3D model (JSmol)	Interactive image
ChemSpider	122157^Y
ECHA InfoCard	100.104.006
EC Number	445-090-6
PubChem CID	138539
UNII	4067E5GBKB^Y
CompTox Dashboard (EPA)	DTXSID2074958
InChI InChI=1S/C6H12O/c1-7-6-4-2-3-5-6/h6H,2-5H2,1H3 Key: SKTCDJAMAYNROS-UHFFFAOYSA-N
SMILES COC1CCCC1
Properties
Chemical formula	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]
Solubility in water	0.011 g/g
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H315, H319
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P302+P352, P303+P361+P353, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P235, P501
NFPA 704 (fire diamond)	2 3 0
Flash point	−1 °C (30 °F; 272 K)
Safety data sheet (SDS)	MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Cyclopentyl methyl ether (CPME), also known as methoxycyclopentane, is a 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 attractive alternative to other ethereal solvents such as tetrahydrofuran (THF), 2-methyltetrahydrofuran (2-MeTHF), dioxane, and 1,2-dimethoxyethane (DME).^[2]

Applications

References

1 2 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.
↑ 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.
↑ Ether compounds and polymerizable compounds and manufacturing methods. By: Kiriki, Satoshi.Aug 3, 2015.JP 2015140302
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ A. Jordan, C.G.J. Hall, L.R. Thorp, H.F. Sneddon (2022), "Replacement of less-preferred dipolar aprotic and ethereal solvents in synthetic organic chemistry with more sustainable alternatives", Chem. Rev., vol. 122, pp. 6749–6794, doi:10.1021/acs.chemrev.1c00672, PMC 9098182{{citation}}: CS1 maint: multiple names: authors list (link)
↑ "Novel hydrophobic ether solvent – Cyclopentyl methyl ether – CPME – Technical Data" (PDF). Zeon Corporation. June 2018. Retrieved 2022-10-20.
↑ D. Rigo, G. Firani, A. Perosa, M. Selva (2019), "Acid-Catalyzed Reactions of Isopropenyl Esters and Renewable Diols: A 100% Carbon Efficient Transesterification/Acetalization Tandem Sequence, from Batch to Continuous Flow", ACS Sustainable Chem. Eng., vol. 7, no. 23, pp. 18810–18818, doi:10.1021/acssuschemeng.9b03359{{citation}}: CS1 maint: multiple names: authors list (link)
↑ U. Azzena, M. Carraro, A.D. Mamuye, I. Murgia, L. Pisano, G. Zedde (2015), "Cyclopentyl methyl ether–NH4X: a novel solvent/catalyst system for low impact acetalization reactions", Green Chem., vol. 17, no. 6, pp. 3281–3284, doi:10.1039/C5GC00465A{{citation}}: CS1 maint: multiple names: authors list (link)
↑ "Zeon Corporation" (PDF). Archived from the original (PDF) on 2011-07-22. Retrieved 2024-08-05.
↑ "Synthetic Applications with Cyclopentyl methyl ether (CPME), Ver. 2.0" (PDF). Zeon Corporation. September 2018. Retrieved 2022-10-20.
↑ U. Azzena, M. Carraro, L. Pisano, S. Monticelli, R. Bartolotta, V. Pace (2019), "Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry", ChemSusChem, vol. 12, no. 1, pp. 40–70, doi:10.1002/cssc.201801768, PMC 6391966{{citation}}: CS1 maint: multiple names: authors list (link)

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