210168-09-5

Basic information

• Product Name: 1-(4-methoxyphenyl)pentane-2,4-dione
• Synonyms: 1-(4-methoxyphenyl)pentane-2,4-dione
• CAS NO: 210168-09-5
• Molecular Weight: 206.241
• Mol File: 210168-09-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(4-methoxyphenyl)pentane-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxyphenyl)pentane-2,4-dione(210168-09-5)
• EPA Substance Registry System: 1-(4-methoxyphenyl)pentane-2,4-dione(210168-09-5)

Safety Data

• Hazardous Substances Data: 210168-09-5(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 15435-71-9 sodium acetylacetonate 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 168210-91-1 1-(4-methoxyphenyl)penta-3,4-dien-2-one 
• 67-64-1 acetone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 14062-18-1 ethyl p-methoxyphenylacetate 

Downstream Products

• 223553-68-2 7-(4-Methoxyphenyl)-[1,6]naphthyridin-5-ol 

Relevant articles and documents

Mercury(II)-catalyzed synthesis of spiro[4.5]decatrienediones in the presence of water

Treatment of the easily available p-methoxybenzyl allenyl ketone 2 or the (p-tert-butyldimethylsiloxybenzyl) allenyl ketone 9 with 1% Hg(ClO4)2 in acetonitrile/water provided good yields of the spiro[4.5]deca-3,6,9- triene-2,8-dione 6c. The Hg(II)-catalyzed addition of water to the allene was much slower, the 1,3-diketone 7 was only a minor side-product. The isomeric o-methoxybenzyl allenyl ketone 12 formed some spiro[4.5]deca-3,7,9-triene- 2,6-dione 13, the side-reactions were the addition of water and a new spirocyclization/dimerization leading to 15.

A new gold-catalyzed C-C bond formation

With a d8 configuration equivalent to palladium(II), gold(III) also catalyzes a number of interesting and effective reactions. The cycloisomerization of allenyl ketones with 1 mol% of catalyst requires about one hour with [PdCl2(MeCN)2] but only a minute with AuCl3; a selective cross coupling of these substrates with Michael acceptors (see scheme) is possible only with the gold catalyst.

A VERSATILE SYNTHESIS OF ARYLACETONES FROM ARYL HALIDES AND ACETYLACETONATE

Reaction of aryl halides with sodium or potassium acetylacetonate in the presence of a copper catalyst affords directly arylacetones resulted from deacetylation of initially formed 3-arylacetylacetones in good yields.