29214-57-1

Basic information

• Product Name: 3-acetylheptane-2,6-dione
• Synonyms: 3-acetylheptane-2,6-dione;3-(3-Oxobutyl)-2,4-pentanedione;2,6-Heptanedione,3-acetyl-
• CAS NO: 29214-57-1
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.20566
• EINECS: 249-517-5
• Mol File: 29214-57-1.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 298.3°Cat760mmHg
• Flash Point: 124.1°C
• Appearance: /
• Density: 1.008g/cm³
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: 1.432
• CAS DataBase Reference: 3-acetylheptane-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetylheptane-2,6-dione(29214-57-1)
• EPA Substance Registry System: 3-acetylheptane-2,6-dione(29214-57-1)

Safety Data

• Hazardous Substances Data: 29214-57-1(Hazardous Substances Data)

Usage

General Description

3-acetylheptane-2,6-dione, also known as acetylacetone, is a yellowish liquid with a fruity odor. It is an organic compound and a β-diketone that is widely used as a reagent in organic synthesis and as a building block in the preparation of various compounds, including pharmaceuticals, agricultural chemicals, and fragrances. Its structure consists of a six-carbon chain with two acetyl groups attached to the second and sixth carbon atoms, giving it its β-diketone properties. It is also commonly employed as a metal chelator due to its ability to form stable complexes with metal ions, making it useful in various industrial and laboratory applications. Additionally, it has been investigated for its potential therapeutic properties due to its antioxidant and anti-inflammatory effects.

InChI:InChI=1/C9H14O3/c1-6(10)4-5-9(7(2)11)8(3)12/h9H,4-5H2,1-3H3

Upstream product

• 78-94-4 methyl vinyl ketone 
• 123-54-6 acetylacetone 
• 3859-41-4 1,3-cyclopentadione 
• 598-32-3 2-hydroxy-3-butene 
• 105-53-3 diethyl malonate 

Downstream Products

• 176237-95-9 heptane-2,3,6-trione 
• 869794-50-3 (3S,8aR)-1-(5,8a-dimethyl-3-phenyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-6-yl)-ethanone 
• 98276-70-1 3,5-diacetyl-1H-pyrazole 
• 291525-43-4 3-diazo-2,6-heptanedione 
• 51742-11-1 6-acetyl-3-methyl-2-cyclohexen-1-one 
• 1721-25-1 1-(2,6-dimethylpyridin-3-yl)ethan-1-one 

Relevant articles and documents

Promiscuous zinc-dependent acylase-mediated carbon-carbon bond formation in organic media

A zinc-dependent acylase, d-aminoacylase from Escherichia. Coli, displays a promiscuous activity to catalyze the carbon-carbon bond formation reaction of 1,3-dicarbonyl compounds to methyl vinyl ketone in organic media. The Royal Society of Chemistry.

Silica gel-mediated catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to highly toxic methyl vinyl ketone without volatilization

Silica gel-mediated Michael addition of 1,3-dicarbonyl compounds to methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) was carried out to give the corresponding adducts in quite excellent yields. The reactions could be carried out without any catalysts and solvents. In addition, highly toxic MVK and EVK could be employed without significant volatilization. Silica gel could be recycled five times without the decrease of the yields.

Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane

Difluorotris(pentafluoroethyl)phosphorane, (C2F5)3PF2, was found to be an active catalyst for the Michael addition reaction of 1,3-β-diketones or β-ketoesters (Michael donors) and linear or cyclic unsaturated ketones (Michael acceptors). The reaction proceeds under mild conditions with low catalyst loading and results in the formation of the Michael addition products in moderate to high yields. The developed protocol does not require the use of a base for the in situ generation of a carbanion (Michael donor).

Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations

One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(iii)/Co(ii) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles. This journal is