1817-90-9

Basic information

• Product Name: Ethyl phenethyl ether
• Synonyms: (2-ethoxyethyl)-benzen;(2-ethoxyethyl)-Benzene;2-PHENYLETHYL METHYL ETHER;METHYL PHENETHYLYL ETHER;METHYL PHENYL ETHYL ETHER;ETHER, METHYL PHENETHYL;FEMA 3198;PHENYL ETHYL METHYL ETHER
• CAS NO: 1817-90-9
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 217-331-3
• Mol File: 1817-90-9.mol

Chemical Properties

• Boiling Point: 194.3°C at 760 mmHg
• Flash Point: 68.1°C
• Appearance: /
• Density: 0.929g/cm³
• Vapor Pressure: 0.623mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: Ethyl phenethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl phenethyl ether(1817-90-9)
• EPA Substance Registry System: Ethyl phenethyl ether(1817-90-9)

Safety Data

• Hazardous Substances Data: 1817-90-9(Hazardous Substances Data)

Usage

Uses

Used in Perfumery Industry:
Ethyl phenethyl ether is used as a solvent for blending and stabilizing fragrances in the perfumery industry. Its pleasant floral odor and ability to dissolve a wide range of aromatic compounds make it an ideal choice for creating long-lasting and complex scents.
Used in Dye Industry:
In the dye industry, Ethyl phenethyl ether is used as a solvent for dissolving and transporting dyes during the dyeing process. Its solubility properties and low toxicity contribute to efficient dyeing processes and reduced environmental impact.
Used in Pharmaceutical Industry:
Ethyl phenethyl ether is utilized as a solvent in the pharmaceutical industry for the synthesis and formulation of various drugs. Its ability to dissolve a wide range of active pharmaceutical ingredients and its low toxicity make it a preferred choice for drug manufacturing processes.
Used in Organic Synthesis:
Ethyl phenethyl ether serves as a versatile intermediate in organic synthesis, particularly in the preparation of various organic compounds, such as phenolic derivatives and other ethers. Its reactivity and stability make it a valuable building block in the synthesis of complex organic molecules.

InChI:InChI=1/C10H14O/c1-2-11-9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Upstream product

• 74-96-4 ethyl bromide 
• 60-12-8 2-phenylethanol 
• 64-67-5 diethyl sulfate 
• 22096-25-9 sodium phenethylate 
• 103-63-9 1-phenyl-2-bromoethane 
• 6921-34-2 benzylmagnesium chloride 
• 3188-13-4 ethyl chloromethyl ether 
• 64-17-5 ethanol 
• 17376-04-4 2-phenethyl iodide 
• 103-45-7 acetic acid phenethyl ester 
• 592-55-2 2-Bromoethyl ethyl ether 
• 591-51-5 phenyllithium 
• 101-97-3 Ethyl 2-phenylethanoate 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 946832-41-3 ethyl 4-nitrophenethyl ether 
• 161368-68-9 ethyl-(2-nitro-phenethyl)-ether 
• 622-24-2 2-phenylethyl chloride 
• 65-85-0 benzoic acid 
• 873412-57-8 2-(2-ethoxyethyl)aniline 

Relevant articles and documents

γ-Ray-induced reduction of sterically hindered alkyl carboxylates with trichlorosilane in the presence of hydrogen chloride. Two-step mechanism for the formation of alkanes via the alkyl chloride

γ-Irradiation of a mixture of 1-adamantyl acetate and trichlorosilane (TCS) in the presence of hydrogen chloride yields adamantane. The first step of this reaction entails cleavage of the alkyloxygen bond by the action of HCl and TCS to give the alkyl chloride. The chloride, in the second step, is dechlorinated by TCS by a known, free-radical mechanism. t-Amyl and benzyl acetates react analogously to 1-adamantyl acetate in this system to give isopentane and toluene, whereas other primary and secondary alkyl derivatives produce the corresponding dialkyl ethers by a known, free-radical mechanism.

Catalytic reductive deoxygenation of esters to ethers driven by hydrosilane activation through non-covalent interactions with a fluorinated borate salt

We report the catalytic and transition metal-free reductive deoxygenation of esters to ethers through the use of a hydrosilane and a fluorinated borate BArF salt as a catalyst. Experimental and theoretical studies support the role of noncovalent interactions between the fluorinated catalyst, the hydrosilane and the ester substrate in the reaction mechanism.

Decomposition of a Β-O-4 lignin model compound over solid Cs-substituted polyoxometalates in anhydrous ethanol: acidity or redox property dependence?

Production of aromatics from lignin has attracted much attention. Because of the coexistence of C–O and C–C bonds and their complex combinations in the lignin macromolecular network, a plausible roadmap for developing a lignin catalytic decomposition process could be developed by exploring the transformation mechanisms of various model compounds. Herein, decomposition of a lignin model compound, 2-phenoxyacetophenone (2-PAP), was investigated over several cesium-exchanged polyoxometalate (Cs-POM) catalysts. Decomposition of 2-PAP can follow two different mechanisms: an active hydrogen transfer mechanism or an oxonium cation mechanism. The mechanism for most reactions depends on the competition between the acidity and redox properties of the catalysts. The catalysts of POMs perform the following functions: promoting active hydrogen liberated from ethanol and causing formation of and then temporarily stabilizing oxonium cations from 2-PAP. The use of Cs-PMo, which with strong redox ability, enhances hydrogen liberation and promotes liberated hydrogen transfer to the reaction intermediates. As a consequence, complete conversion of 2-PAP (>99%) with excellent selectivities to the desired products (98.6% for phenol and 91.1% for acetophenone) can be achieved.

A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives

A versatile iridium(III) metallacycle catalysed rapidly and selectively the reduction of a large array of challenging esters and carboxylic acids as well as various ketones and aldehydes. The reactions proceeded in high yields at room temperature by hydrosilylation followed by desilylation. Although the reactions of various aldehydes and ketones resulted exclusively in alcohols, the hydrosilylation of esters led to alcohols or ethers, depending on the type of substrate. Regarding the carboxylic acids, again the nature of the reagent controlled the outcome of the hydrosilylation reaction, either alcohols or aldehydes being formed.

Selective Hydrosilylation of Esters to Aldehydes Catalysed by Iridium(III) Metallacycles through Trapping of Transient Silyl Cations

The combination of an iridium(III) metallacycle and 1,3,5-trimethoxybenzene catalyses rapidly and selectively the reduction of esters to aldehydes at room temperature with high yields through hydrosilylation followed by hydrolysis. The ester reduction involves the trapping of transient silyl cations by the 1,3,5-trimethoxybenzene co-catalyst, supposedly by formation of an arenium intermediate whose role was addressed by DFT calculations.

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

The nucleophilic addition of methanol and other alcohols to 1,1-diphenylethylene (1) and styrene (6) into the Markovnikov- and anti-Markovnikov-type products was selectively achieved with 1-(N,N-dimethylamino)pyrene (Py) and 1,7-dicyanoperylene-3,4:9,10-tetracarboxylic acid bisimide (PDI) as photoredox catalysts. The regioselectivity was controlled by the photocatalyst. For the reductive mode towards the Markovnikov-type regioselectivity, Py was applied as photocatalyst and triethylamine as electron shuttle. This approach was also used for intramolecular additions. For the oxidative mode towards the anti-Markovnikov-type regioselectivety, PDI was applied together with Ph-SH as additive. Photocatalytic additions of a variety of alcohols gave the corresponding products in good to excellent yields. The proposed photocatalytic electron transfer mechanism was supported by detection of the PDI radical anion as key intermediate and by comparison of two intramolecular reactions with different electron density. Representative mesoflow reactor experiments allowed to significantly shorten the irradiation times and to use sunlight as "green"light source.

Step-economy etherification of acylated alcohols

An efficient and convenient protocol has been developed for ether bond formation in mild conditions. A mixture of primary/secondary ester and allylic/benzylic halide in tetrahydrofuran was treated with KOtBu at room temperature to give ether in high yield. This step economic method enabled direct alkylation of the acyl group masked O-nucleophiles. Application of this method in carbohydrate synthesis was feasible and chemo-selectivity can be achieved.

SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1

Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.

Reductive etherification of aldehydes photocatalyzed by dicarbonyl pentamethylcyclopentadienyl iron complexes

The reductive etherification of aldehydes can be performed by the reaction with dialkylmethylsilanes in the presence of new iron(II) piano-stool catalysts of general formula Cp*Fe(CO)2Ar (Cp * = η5-C5Me5; Ar = Ph, 4-C6H4OCH3, 4-C6H4CH 3, Fc). This transformation is promoted by UV light and affords a simple route for the preparation of unsymmetrical alkyl ethers.

Synthesis of ethers from esters via Fe-catalyzed hydrosilylation

Triiron dodecacarbonyl allows for the selective reduction of esters into the corresponding ethers. This protocol has a wide substrate scope. In addition, cholesteryl pelarogonate has been reduced under the reaction conditions with an excellent yield.