Cyclopentyl methyl ether

Base Information

• Chemical Name: Cyclopentyl methyl ether
• CAS No.: 5614-37-9
• Molecular Formula: C6H12O
• Molecular Weight: 100.161
• Hs Code.: 2909 20 00
• European Community (EC) Number: 445-090-6,611-360-9
• UNII: 4067E5GBKB
• DSSTox Substance ID: DTXSID2074958
• Nikkaji Number: J191.958J
• Wikipedia: Cyclopentyl_methyl_ether
• Wikidata: Q3333694
• Mol file: 5614-37-9.mol

Synonyms:Ether,cyclopentyl methyl (7CI,8CI);Methoxycyclopentane;Methyl cyclopentyl ether;

Chemical Property of Cyclopentyl methyl ether

Chemical Property:

• Vapor Pressure: 34.6mmHg at 25°C
• Melting Point: -140°C
• Refractive Index: 1.423
• Boiling Point: 105.3 °C at 760 mmHg
• Flash Point: 6.5 °C
• PSA: 9.23000
• Density: 0.86 g/cm³
• LogP: 1.57540
• Storage Temp.: Flammables area
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: Miscible with water, alcohols, ketones and hydrocarbons.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 100.088815002
• Heavy Atom Count: 7
• Complexity: 46.1

Purity/Quality:

98% ^*data from raw suppliers

Cyclopentyl methyl ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; Xn
• Hazard Codes: F,Xn
• Statements: 11-22-36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1CCCC1
• Uses: Cyclopentyl methyl ether (CPME) is an alternative to ether solvents such as THF, diethyl ether, and MTBE with a higher resistance to peroxide formation. The more environmentally conservative CPME solvent replaces hazardous solvents in order to achieve sustainability and reduce environmental and operational costs. CPME offers considerable potential and advantage as a direct replacement for CH2Cl2 in binary eluents using MeOH as the modifier with MeOH-DMC and i-PrOH-EtOAc. Cyclopentyl methyl ether is a hydrophobic ether solvent widely used in Grignard reaction, Friedel-Crafts reaction, Claisen condensation and Beckmann reaction. It plays an important role in extraction and polymerization reactions as well as in surface coatings. It is considered as a replacement for tetrahydrofuran, methyl tert-butyl ether, dioxane and other existing ether solvents due to its excellent properties like high boiling point and relative stability under acidic and basic conditions. Greener alternative solvent in reactions containing the following reagents:Alkali agentsLewis acid-mediated reactionsOrganometallicReduction and OxidationTransition metal catalystsAzeotropic water removalCan also be used in extraction, polymerization, crystallization and surface coatings.The toxicological assessment of cyclopentyl methyl ether (CPME) as a green solvent.

Technology Process of Cyclopentyl methyl ether

There total 19 articles about Cyclopentyl methyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.4%

methanol (67-56-1) + Cyclopentanol (96-41-3) → cyclopentyl methyl ether (5614-37-9)

Guidance literature:

With large-pore aluminosilicate zeolite ZSM-5 with Si\Al ratio of 40; at 100 ℃; for 6h; Reagent/catalyst; Temperature;

DOI:10.1016/j.apcata.2021.118122

Reference yield: 75.5%

methanol (67-56-1) + cyclopentene (142-29-0) → cyclopentyl methyl ether (5614-37-9)

Guidance literature:

With dry acidic ion-exchange resin (SPC₁₀₈); at 90 ℃; for 7h; under 760 Torr;

Reference yield: 63.0%

trimethyl phosphite (512-56-1) + Cyclopentanol (96-41-3) → cyclopentyl methyl ether (5614-37-9)

Guidance literature:

With PPA; at 180 - 190 ℃; for 2h;

DOI:10.3891/acta.chem.scand.52-1223

upstream raw materials:

Cyclopentyl bromide

sodium methylate

cyclopentyl chloride

sodium cyclopentanolate

Downstream raw materials:

Cyclopentyl Nitrate

cyclopentanone

N-benzylidene-2-methoxy-1-(1-methoxycyclopentyl)-2-oxoethanamine N-oxide

N-benzylidene-3-(cyclopentyloxy)-1-methoxy-1-oxopropan-2-amine N-oxide

Refernces

Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents

10.1016/j.tet.2021.131935

The study investigates the reactivity and selectivity of alkyl-substituted Li-phenolates with benzyl bromide (BnBr) in various solvent conditions, particularly in anhydrous environments. The researchers found that ortho-selective alkylation could be achieved in non-aqueous solvents like cyclopentyl methyl ether (CPME) and toluene, with the addition of ether or alcohol additives, leading to the formation of o-Bn-substituted alkyl cyclohexadienones with yields up to 92% and an o/p ratio up to 90/1. The method is sensitive to the structure of phenols, and optimal conditions may be needed for each phenolate. The alkylation reaction is catalyzed by ethers and alcohols, and the researchers are exploring the possibility of introducing asymmetric induction to the dearomatization reaction.

A new class of organocatalysts: Sulfenate anions

10.1002/anie.201405996

The study introduces sulfenate anions as a new class of organocatalysts, demonstrating their ability to catalyze the conversion of benzyl halides into trans-stilbenes under basic conditions with yields up to 99%. The researchers hypothesized that sulfenate anions, known for their reactivity, could serve as catalysts based on their behavior in a palladium-catalyzed conversion of aryl benzyl sulfoxides into diaryl sulfoxides. They optimized the reaction conditions using benzyl phenyl sulfoxide as the catalyst precursor and KOtBu as the base in cyclopentyl methyl ether (CPME) solvent at 80°C. The study explored various benzyl halides, finding that benzyl chlorides were more effective than bromides. The scope of the transformation included substrates with alkyl, halide, and fluorine substituents, achieving good to excellent yields. Mechanistic studies supported the intermediacy of sulfenate anions and identified the deprotonated sulfoxide as the catalyst's resting state. The research also demonstrated the scalability of the reaction and the potential use of different sulfoxide precatalysts, including DMSO.

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