52711-59-8

Basic information

• Product Name: 1,4-Naphthalenedione, 2-methyl-3-(phenylmethyl)-
• CAS NO: 52711-59-8
• Molecular Formula: C18H14O2
• Molecular Weight: 262.308
• Mol File: 52711-59-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1,4-Naphthalenedione, 2-methyl-3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Naphthalenedione, 2-methyl-3-(phenylmethyl)-(52711-59-8)
• EPA Substance Registry System: 1,4-Naphthalenedione, 2-methyl-3-(phenylmethyl)-(52711-59-8)

Safety Data

• Hazardous Substances Data: 52711-59-8(Hazardous Substances Data)

Upstream product

• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 100-51-6 benzyl alcohol 
• 106133-55-5 2-(α-chloro-benzyl)-3-methyl-[1,4]naphthoquinone 
• 58-27-5 menadione 
• 316801-21-5 benzyl p-methylphenyl telluride 
• 100-39-0 benzyl bromide 
• 614-45-9 tert-Butyl peroxybenzoate 
• 33440-68-5 2-benzyl-1,4-naphthoquinone 
• 108-88-3 toluene 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 
• 130-15-4 [1,4]naphthoquinone 
• 103-80-0 phenylacetyl chloride 
• 60505-21-7 3-phenyl-1-(2-(prop-2-yn-1-yloxy)phenyl)propan-1-one 
• 10304-09-3 potassium oxalate monomethyl ester 

Downstream Products

• 27402-99-9 3,3'-Dibenzyl-2,2'-aethylen-di-1,4-naphthochinon 

Relevant articles and documents

Bioinspired Photoredox Benzylation of Quinones

3-Benzylmenadiones were obtained in good yield by using a blue-light-induced photoredox process in the presence of Fe(III), oxygen, and γ-terpinene acting as a hydrogen-atom transfer agent. This methodology is compatible with a wide variety of diversely substituted 1,4-naphthoquinones as well as various cheap, readily available benzyl bromides with excellent functional group tolerance. The benzylation mechanism was investigated and supports a three-step radical cascade with the key involvement of the photogenerated superoxide anion radical.

Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant

A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction.

Radical Benzylation of Quinones via C-H Abstraction

Herein we report the development of radical benzylation reactions of quinones using Selectfluor and catalytic Ag(I) initiators. The reaction is believed to proceed via a C-H abstraction mechanism after Ag(I)-mediated reduction of Selectfluor. This reaction occurs under mild conditions and is effective for a variety of quinones and radical precursors bearing primary benzylic carbons. The use of preformed Ag(4-OMePy)2NO3 as a catalyst proved effective in improving the reaction efficiency by reducing unwanted degradation pathways available to Selectfluor.