446312-09-0

Basic information

• Product Name: 1,3-Cyclopentanedione, 2-(bromomethyl)-2-(4-methoxyphenyl)-
• CAS NO: 446312-09-0
• Molecular Formula: C13H13BrO3
• Molecular Weight: 297.148
• Mol File: 446312-09-0.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Cyclopentanedione, 2-(bromomethyl)-2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclopentanedione, 2-(bromomethyl)-2-(4-methoxyphenyl)-(446312-09-0)
• EPA Substance Registry System: 1,3-Cyclopentanedione, 2-(bromomethyl)-2-(4-methoxyphenyl)-(446312-09-0)

Safety Data

• Hazardous Substances Data: 446312-09-0(Hazardous Substances Data)

Upstream product

• 446312-07-8 2-[2-bromo-1-methoxy-1-(4-methoxy-phenyl)-ethyl]-2-trimethylsilanyloxy-cyclobutanone 
• 80336-70-5 2-bromo-1,1-dimethoxy-1-(4-methoxyphenyl)ethane 

Downstream Products

• 59007-04-4 2-(4-methoxyphenyl)-1,4-hydroquinone 
• 479075-37-1 2-(4-methoxy-phenyl)-cyclohexane-1,4-dione 

Relevant articles and documents

Novel access to cyclohexane-1,4-diones and 1,4-hydroquinones via radical 1,2-acyl rearrangement on 2-(halomethyl)cyclopentane-1,3-diones using cobaloxime-mediated electroreduction or tributyltin hydride

A new preparative access to synthetically useful cyclohexane-1,4-diones 2 and their oxidized analogues, hydroquinones 3, with the option of introducing alkyl and aryl substituents, was developed by radical 1,2-acyl rearrangement on 2-(halomethyl)cyclopentane-1,3-diones 1, accessible from 1,2-bis(trimethylsiloxy)cyclobutene and α-bromo ketone dimethyl acetals. The electroreduction of monoacetals of 1 in the presence of cobaloxime as a catalyst afforded the cyclohexane-1,4-dione monoacetals in good yields. The Bu3SnH-reduction of 2-aryl 1 under refluxing in benzene effected the rearrangement, affording 2, and when the reaction was prolonged, aromatization to 3 proceeded in moderate yields.