6630-18-8

Basic information

• Product Name: 4-BENZYLOXYANISOLE
• Synonyms: Ether, benzyl p-methoxyphenyl;4-BENZYLOXYANISOLE;(4-Methoxyphenyl)benzyl ether;1-Methoxy-4-benzyloxybenzene;4-Methoxy-1-(benzyloxy)benzene;4-Methoxyphenylbenzyl ether;Benzyl p-methoxyphenyl ether;Benzyl(4-methoxyphenyl) ether
• CAS NO: 6630-18-8
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.26
• Mol File: 6630-18-8.mol
• Article Data: 50

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 334.3 °C at 760 mmHg
• Flash Point: 134.9 °C
• Appearance: /
• Density: 1.081 g/cm³
• Vapor Pressure: 0.000251mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BENZYLOXYANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXYANISOLE(6630-18-8)
• EPA Substance Registry System: 4-BENZYLOXYANISOLE(6630-18-8)

Safety Data

• Hazardous Substances Data: 6630-18-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxyanisole is used as a pharmaceutical intermediate for the synthesis of various medications. Its aromatic ether group provides reactivity and functionality that are essential in the development of new drugs.
Used in Organic Synthesis:
4-Benzyloxyanisole is used as a reagent in organic synthesis processes. Its unique structure allows for the creation of a wide range of chemical compounds, making it a valuable component in the field of chemistry.

InChI:InChI=1/C14H14O2/c1-15-13-7-9-14(10-8-13)16-11-12-5-3-2-4-6-12/h2-10H,11H2,1H3

Upstream product

• 29368-59-0 p-methoxyphenolate 
• 100-44-7 benzyl chloride 
• 1200-06-2 4-methoxyphenyl acetate 
• 100-39-0 benzyl bromide 
• 1122-95-8 sodium 4-methoxyphenolate 
• 100-17-4 para-methoxynitrobenzene 
• 100-51-6 benzyl alcohol 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 150-76-5 4-methoxy-phenol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 7700-27-8 4-chlorophenyl benzyl ether 
• 87100-28-5 pinacol benzylboronate 
• 42790-42-1 4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride 

Downstream Products

• 92495-78-8 4-benzyl-2-methoxyphenol 
• 130570-56-8 4-benzyloxy-1-methoxy-2-nitro-benzene 
• 82780-78-7 1-benzyloxy-4-methoxy-2-nitro-benzene 
• 135505-53-2 N-(4-Methoxyphenyl)-N-phenyl-1-naphthalenemethanamine 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 
• 73010-55-6 4-(benzyloxy)-4-methoxy-2,5-cyclohexadien-1-one 
• 150-76-5 4-methoxy-phenol 
• 103-16-2 4-Benzyloxyphenol 
• 95-71-6 2-methylbenzene-1,4-diol 
• 38940-06-6 2-benzyl-4-methoxyphenol 
• 123-31-9 hydroquinone 
• 1523-19-9 4-methoxyphenyl benzoate 
• 65-85-0 benzoic acid 
• 848006-80-4 2-(benzyloxy)-5-methoxyterephthalaldehyde 

Relevant articles and documents

Aromatic ether compound or the sulfhydryl compound

[Problem] Aromatic ether compounds and aromatic sulfide compound of this new technology to[Solution] In general formula (1a), (1b), (1c) palladium or nickel compound or a phosphine compound represented by the compound comprising a transition metal compound in the presence of a transition metal catalyst, (A1) is represented by compounds having hydroxy carbon C a-OH or (A2) with a compound represented by the sulfhydryl carbon C a-SH, nitro group (- NO2 ) To react with an aromatic nitro compound (B), (A1) to the compound of the aromatic nitro compound (C1) or the reaction product of an aromatic ether compounds (B) hetero coupling (A2) of the compounds of the reaction product of an aromatic sulfide compound of an aromatic nitro compound (C2) generating (B) hetero coupling characterized by comprising the step of, aromatic ether compounds or aromatic sulfide compound. [Drawing] no

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

α-Lithiobenzyloxy as a Directed Metalation Group in ortho-Lithiation Reactions

The α-lithiobenzyloxy group, easily generated from aryl benzyl ethers by selective α-lithiation with t-BuLi at low temperature, behaves as a directed metalation group (DMG) providing a direct access to o-lithiophenyl α-lithiobenzyl ethers. This ortho-directing effect is reinforced in substrates bearing an additional methoxy group at the meta position. The generated dianions can be reacted with a selection of electrophiles including carboxylic esters and dihalosilanes or germanes, which afford interesting benzofuran, sila(germa)dihydrobenzofuran, and silachroman derivatives from simple aryl benzyl ethers.

Pd(OAc)2-catalyzed synthesis of benzyl phenyl ether derivatives with H2O2 as an oxidant in neat water

A new protocol for Pd(OAc)2-catalyzed reactions of different benzyl bromides and various arylboronic acids has been developed to form functionalized benzyl phenyl ethers. This method represents the first instance where arylboronic acid is used as a reaction substrate for benzyl phenyl ether synthesis with H2O2 as the green oxidant under atmospheric oxygen and pure H2O as an environmental friendly solvent without the requirement for phosphine- and N-based ligands, remarkable functional group tolerance, and considerable yield.

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.

BIS-BENZIMIDAZOLE COMPOUNDS AND METHODS OF USING SAME

Provided herein are compounds and methods for modulating abnormal repeat expansions of gene sequences. More particularly, provided are inhibitors of RNA and the uses of such inhibitors in regulating nucleotide repeat expansions, e.g., to treat Myotonic Dystrophy Type 1 (DM1 ), Myotonic Dystrophy Type 2 (DM2), Fuchs dystrophy, Huntington Disease, Amyotrophic Lateral Sclerosis, or Frontotemporal Dementia.

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Constitutional Isomers of Pentahydroxy-Functionalized Pillar[5]arenes: Synthesis, Characterization, and Crystal Structures

We herein report the preparation of constitutional isomers of pentahydroxy-functionalized pillar[5]arenes via the deprotection of their benzylated derivatives by catalytic hydrogenation. The structures of the obtained isomers were then established using single crystal X-ray diffraction. We also found that the yield distribution of the different constitutional isomers was dependent on the nature of the substitution, as revealed by HPLC analysis of the crude mixture. Finally, further characterization of the separated constitutional isomers indicated that they possess different melting points, NMR spectra, crystal structures, and stacking patterns in the solid state.

MCM-41-immobilized 1,10-phenanthroline-copper(i) complex: A highly efficient and recyclable catalyst for the coupling of aryl iodides with aliphatic alcohols

A heterogeneous C-O coupling reaction between aryl iodides and aliphatic alcohols was achieved in neat alcohol or toluene at 110 °C in the presence of 10 mol% of the MCM-41-immobilized 1,10-phenanthroline-copper(i) complex [MCM-41-1,10-phen-CuI] with Cs2CO3 as a base, yielding a variety of aryl alkyl ethers in good to excellent yields. The new heterogeneous copper catalyst can easily be prepared by a simple procedure from commercially available and inexpensive reagents, and recovered by filtration of the reaction solution and recycled at least 8 times without significant loss of activity.