834-25-3

Basic information

• Product Name: benzyl p-tolyl ether
• Synonyms: benzyl p-tolyl ether;Benzyl p-cresyl ether;1-(Benzyloxy)-4-methylbenzene;4-Methyl-1-benzyloxybenzene;p-Tolylbenzyl ether
• CAS NO: 834-25-3
• Molecular Formula: C₁₄H₁₄O
• Molecular Weight: 198.26036
• EINECS: 212-636-8
• Mol File: 834-25-3.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 308.3°C at 760 mmHg
• Flash Point: 120.4°C
• Appearance: /
• Density: 1.041g/cm³
• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: benzyl p-tolyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl p-tolyl ether(834-25-3)
• EPA Substance Registry System: benzyl p-tolyl ether(834-25-3)

Safety Data

• Hazardous Substances Data: 834-25-3(Hazardous Substances Data)

Usage

General Description

Benzyl p-tolyl ether is an organic compound with the chemical formula C14H14O. It is a colorless liquid that is commonly used as a solvent in various industrial processes and can be found in some consumer products. Benzyl p-tolyl ether is also used as a building block in the synthesis of pharmaceuticals and other organic compounds. It has a sweet, floral odor and is flammable, making it important to handle with care. The compound is often used as a fragrance ingredient and in the production of flavorings and perfumes.

InChI:InChI=1/C14H14O/c1-12-7-9-14(10-8-12)15-11-13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 1192-96-7 potassium p-cresolate 
• 100-44-7 benzyl chloride 
• 1121-70-6 sodium 4-methylphenoxide 
• 108-88-3 toluene 
• 22900-27-2 benzylphenylmethyl sulfonium fluoroborate 
• 106-44-5 p-cresol 
• 100-39-0 benzyl bromide 
• 624-31-7 4-tolyl iodide 
• 100-51-6 benzyl alcohol 
• 5720-05-8 4-methylphenylboronic acid 
• 754226-40-9 4,4,5,5,-tetramethyl-2-[4-(phenylmethoxy)phenyl]-1,3,2-dioxaborolane 
• 74-88-4 methyl iodide 
• 6793-92-6 p-benzyloxyphenylbromide 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 15539-77-2 4-nitrobenzyl nitrate 
• 609-93-8 2,6-dinitro-p-cresol 
• 100-52-7 benzaldehyde 
• 106-44-5 p-cresol 
• 1517-63-1 4-methylphenyl(phenyl)methanol 
• 108-88-3 toluene 
• 36441-31-3 1-benzyl-2-naphthol 
• 716-96-1 2-benzyl-4-methylphenol 
• 51009-90-6 2,7-dimethyl-9-phenyl-xanthene 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 6939-75-9 benzyl levulinate 
• 36803-96-0 2-(benzyloxy)-5-methylphenyl acetate 
• 82166-21-0 methyl cyclohexane 

Relevant articles and documents

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

Alkyl-substituted Li-phenolates with BnBr in water solution lead to a mixture of o- and p-Bn-substituted phenols together with a substantial amount of phenol Bn ether. In CPME, and especially in toluene with 1–2 equivalents of ether or alcohol additives, ortho-selective alkylation is achieved. In the case of o,o,p-tri- and o,o-di-substituted phenols dearomatization occurs affording o-Bn-substituted alkyl cyclohexadienones with yields up to 92% with an o/p ratio up to 90/1.

Synthesis of 6 H-Benzo[ c]chromene Scaffolds from O-Benzylated Phenols through a C-H Sulfenylation/Radical Cyclization Sequence

S-Aryl dibenzothiophenium salts, obtained through a highly regioselective C-H sulfenylation of o-benzyl-protected phenols, are used as precursors of 6H-benzo[c]chromenes. The reaction starts with a photocatalytically triggered single-electron transfer to the sulfonium salt, which promotes the formation of an aryl radical via selective mesolitic cleavage of the S-Arexo bond. Mechanistic studies reveal that this initial radical species cyclizes following a kinetically favored 5-exo-trig pathway. Subsequent ring expansion, favored by rearomatization, delivers the desired tricyclic systems.

Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.