54894-37-0

Basic information

• Product Name: [(2-phenylethoxy)methyl]benzene
• Synonyms: [(2-phenylethoxy)methyl]benzene;Benzyl-(2-phenethyl) ether;(Phenethyloxymethyl)benzene;Benzyl(phenethyl) ether;Benzylphenethyl ether;Phenethylbenzyl ether;Benzene, ((2-phenylethoxy)methyl)-;Benzyl 2-phenylethyl ether
• CAS NO: 54894-37-0
• Molecular Formula: C₁₅H₁₆O
• Molecular Weight: 212.28694
• EINECS: 259-386-6
• Mol File: 54894-37-0.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 303.1°C at 760 mmHg
• Flash Point: 145.8°C
• Appearance: /
• Density: 1.031g/cm³
• Vapor Pressure: 0.0017mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: [(2-phenylethoxy)methyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(2-phenylethoxy)methyl]benzene(54894-37-0)
• EPA Substance Registry System: [(2-phenylethoxy)methyl]benzene(54894-37-0)

Safety Data

• Hazardous Substances Data: 54894-37-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 30, p. 2467, 1974 DOI: 10.1016/S0040-4020(01)97118-2Tetrahedron Letters, 36, p. 3465, 1995 DOI: 10.1016/0040-4039(95)00527-J

InChI:InChI=1/C15H16O/c1-3-7-14(8-4-1)11-12-16-13-15-9-5-2-6-10-15/h1-10H,11-13H2

Upstream product

• 22096-25-9 sodium phenethylate 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 60-12-8 2-phenylethanol 
• 53772-44-4 benzyloxydiphenylphosphine 
• 952057-61-3 N-phenyl-2,2,2-trifluoroacetimidoyl chloride 
• 100-39-0 benzyl bromide 
• 4410-99-5 2-mercaptophenylethane 
• 1207372-96-0 o-[2-(4-methoxyphenyl)ethynyl]benzoic acid benzyl ester 
• 103-45-7 acetic acid phenethyl ester 
• 100-42-5 styrene 
• 100-51-6 benzyl alcohol 
• 864298-72-6 benzyl P,P-diphenyl-N-(diphenylphosphoryl)phosphinimidate 
• 864298-78-2 benzyl N-(p-tolylsulfonyl)diphenylphosphinimidate 

Downstream Products

• 24330-46-9 2-phenylethyl nitrite 
• 122-78-1 phenylacetaldehyde 
• 100-52-7 benzaldehyde 
• 60-12-8 2-phenylethanol 
• 831-91-4 Benzyl phenyl sulfide 
• 13865-49-1 [2-(phenylsulfanyl)ethyl]benzene 
• 103-45-7 acetic acid phenethyl ester 
• 620-47-3 1-methyl-3-(phenylmethyl)-benzene 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 
• 713-36-0 2-benzyltoluene 
• 65-85-0 benzoic acid 
• 100-41-4 ethylbenzene 
• 95843-98-4 2-(benzyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 108-88-3 toluene 

Relevant articles and documents

Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis

Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.

Vanadium-Catalyzed Oxidative Debenzylation of O-Benzyl Ethers at ppm Level

An advantageous methodology for the oxidative debenzylation of ethers has been developed. Very low amounts of a catalyst system based on vanadyl acetylacetonate and a triazole type pincer ligand allow the selective oxidative cleavage of a number of O-benzyl ethers in the presence of oxygen as the sole oxidant. The methodology tolerates a number of functional groups such as halo-, alkoxy-, or trifluoromethylarenes, alkyne, alkene, ether, and acetal units. Large-scale deprotections can be also carried out by the optimized procedure, which is amenable to enantioenriched reactants as well. (Figure presented.).

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.