17407-24-8

Basic information

• Product Name: 9-(4-methoxybenzyl)anthracene
• Synonyms: 9-(4-methoxybenzyl)anthracene
• CAS NO: 17407-24-8
• Molecular Weight: 298.384
• Mol File: 17407-24-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 9-(4-methoxybenzyl)anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(4-methoxybenzyl)anthracene(17407-24-8)
• EPA Substance Registry System: 9-(4-methoxybenzyl)anthracene(17407-24-8)

Safety Data

• Hazardous Substances Data: 17407-24-8(Hazardous Substances Data)

Upstream product

• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 53781-03-6 10-(4-methoxy-benzyliden)-anthrone 
• 90-44-8 anthracen-9(10H)-one 
• 41199-59-1 (9,10-Dihydro-anthracen-9-yl)-(4-methoxy-phenyl)-methanol 
• 77032-84-9 anthracen-9-yl-(4-methoxy-phenyl)-methanol 
• 85865-15-2 C₂₂H₁₇LiO 
• 85865-16-3 C₂₂H₁₇NaO 
• 77032-88-3 9-[Chloro-(4-methoxy-phenyl)-methyl]-anthracene 
• 1468-95-7 9-hydroxymethylanthracene 
• 100-66-3 methoxybenzene 
• 882529-82-0 trans-9,10-dihydro-10-(4-methoxybenzyl)-anthracen-9-ol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 41199-50-2 (9,10-Dihydro-anthracen-9-yl)-(4-methoxy-phenyl)-methanone 
• 579504-79-3 10-(4-methoxybenzyl)-9(10H)-anthracenone 

Downstream Products

• 119533-04-9 diethyl-[2-(4-[9]anthrylmethyl-phenoxy)-ethyl]-amine 
• 56181-27-2 1,4-Dimethoxy-9-(4-methoxybenzyl)-triptycen 
• 102242-15-9 4-[9]Anthrylmethyl-phenol 

Relevant articles and documents

Acid-catalyzed cyclization of anthracenol derivatives to homotriptycenes

10-Benzyl-9,10-dihydroanthracen-9-ols, having high electron densities in the benzene ring, exhibit in the presence of acid a transannular ring closure to the corresponding homotriptycenes in almost quantitative yields. Since the starting compounds are easily accessible from 9(10H)-anthracenone, this process represents the most facile route to such pentacyclic systems. An electron-releasing methoxy group enables the intramolecular electrophilic substitution in its para position. In the absence of such an activation, a number of alternative processes can occur, namely the acid-catalyzed dehydration to anthracene derivatives with (R ≠ H) or without (R = H) rearrangement or a disproportionation reaction of the secondary alcohol to the corresponding ketone and hydrocarbon.

Protonation and Alkylation of Ambident (9-Anthryl)arylmethyl Anions

We have investigated the protonation of ambident (9-anthryl)arylmethylsodiums (Na-2) and -lithiums (Li-2) (substituent =p-Me, p-Me, H, m-F) with various oxygen and carbon acids in tetrahydrofuran to give a mixture of the anthracene derivatives 3a-d and the 9,10-dihydroanthracenes 4a-d.Product compositions were dramatically influenced by the substituent electronic effects of the carbanions 2 and the acidities of the proton donors.In the protonation with the oxygen proton donors the change of the countercation 2 and the addition of hexamethylphosphoramide also exerted remarkable effects on the 3:4 ratio, whereas these two factors were not important in the case of the carbon acids.This fact would be interpreted as the extent of coordination of oxygen acids to metal cations being important in determining protonation regiochemistry.The reaction of (9-anthryl)arylmethyl anions (2a-d) with a series of aliphatic and benzylic halides gave a mixture of two cross-coupling products, 7 (coupling at C-α) and 8 (coupling at C-10), and/or dimers, 5 Cα-C10 coupling) and 6 (C10-C10 coupling), the composition being influenced by the substituent electronic effects of the carbanions 2 and structure of the alkyl groups of the halides.The leaving group effects also have a significant influence on the product composition.Using dependence (or independence) of the product composition on the electronic effects of the substituent of 2 as a tool to differentiate the reaction mechanisms, we have attempted to rationalize the apparently complicated alkylation of the carbanions 2.

Reactions of (9-Anthryl)arylmethyl Chloride and Its Homologues with Nucleophiles under Solvolytic Conditions. Notable Effects of Reaction Conditions and Substituents on the Reaction Sites

The reactions of (9-anthryl)arylmethyl chlorides 2a-e (the substituents are p-MeO, p-Me, H, p-Cl, and m-Cl), the corresponding bromides 3b-d (the substituents are p-Me, H, and p-Cl), and the antimonate salts 4b-e (the substituents are p-Me, H, p-Cl, and m