1703-51-1

Basic information

• Product Name: 2,5-HEPTANEDIONE
• Synonyms: 2,5-HEPTANEDIONE;Heptan-2,5-dione;heptane-2,5-dione
• CAS NO: 1703-51-1
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• Mol File: 1703-51-1.mol

Chemical Properties

• Boiling Point: 208.3 °C at 760 mmHg
• Flash Point: 74.3 °C
• Appearance: /
• Density: 0.926 g/cm³
• Vapor Pressure: 0.216mmHg at 25°C
• Refractive Index: 1.413
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,5-HEPTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-HEPTANEDIONE(1703-51-1)
• EPA Substance Registry System: 2,5-HEPTANEDIONE(1703-51-1)

Safety Data

• Hazardous Substances Data: 1703-51-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 5309, 1971 DOI: 10.1021/ja00749a086The Journal of Organic Chemistry, 39, p. 259, 1974 DOI: 10.1021/jo00916a037Tetrahedron Letters, 23, p. 2237, 1982

InChI:InChI=1/C7H12O2/c1-3-7(9)5-4-6(2)8/h3-5H2,1-2H3

Upstream product

• 78270-18-5 ethyl 2-acetyl-4-oxohexanoate 
• 1703-52-2 2-ethyl-5-methylfuran 
• 917-64-6 methyl magnesium iodide 
• 18022-51-0 1-methyl-2-methylenecyclobutanol 
• 42397-25-1 5-nitroheptan-2-one 
• 53626-82-7 6-bromo-hept-6-en-3-one 
• 123-38-6 propionaldehyde 
• 78-94-4 methyl vinyl ketone 
• 32776-08-2 3-(1-diethylamino-propylidene)-5-methyl-3H-furan-2-one 
• 72128-81-5 1-(3-ethyl-4,5-dihydro-5-isoxazolyl)-1-ethanone 
• 110-43-0 n-pentyl methyl ketone 
• 22592-18-3 hept-5-yn-2-one 
• 36678-43-0 (E)-hept-4-en-2-one 
• 82989-34-2 2-Methyl-2-((Z)-3-methylsulfanyl-pent-2-enyl)-[1,3]dioxolane 

Downstream Products

• 109734-35-2 4-(2-ethyl-5-methyl-pyrrol-1-yl)-2-isopropyl-5-methyl-phenol 
• 156000-12-3 2-methyl-2-<3'(1,3-dithiolanyl)pentyl>thiazolidine 
• 156000-11-2 2-ethyl-2-<3'(1,3-dithiolanyl)butyl>thiazolidine 
• 294176-79-7 1-(cyanomethyl)-2,5-dimethylpyrrol 
• 1260147-07-6 C₁₄H₁₇N 
• 1260147-23-6 C₁₄H₁₇N 
• 1121-05-7 2,3-dimethylcyclopent-2-enone 

Relevant articles and documents

REGIOSELECTIVE OXIDATION OF INTERNAL OLEFINS BEARING NEIGHBORING OXYGEN FUNCTIONS BY MEANS OF PALLADIUM CATALYSTS. A DIRECT PREPARATION OF γ-KETO ESTERS AND 1,4-DIKETONES FROM β,γ-UNSATURATED ESTERS AND KETONES

γ-Keto esters and 1,4-diketones were prepared by the palladium-catalyzed regioselective oxidation of β,γ-unsaturated esters and ketones.The best yields were obtained when the reaction was carried out using PdCl2/CuCl/O2 catalyst system in aqueous dioxane.

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.

Pheromone synthesis. Part 262: Determination of the absolute configuration of the female sex pheromone [(1S,2S)-(?)-(1,2-dimethyl-3-methylenecyclopentyl) acetaldehyde] of the pineapple mealybug (Dysmicoccus brevipes) by synthesis coupled with X-ray analysis

The enantiomers of (anti-1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde, one of which is the female sex pheromone of the pineapple mealybug (Dysmicoccus brevipes), were synthesized. Chirality was introduced by means of lipase-catalyzed asymmetric acetylation of (±)-2,3-dimethyl-2-cyclopenten-l-ol. X-ray analysis of (?)-camphanate ester of (1S,2S)-(?)-2-(1,2-dimethyl-3-methylenecyclopentyl)ethanol confirmed its (1S,2S)-absolute configuration. The natural pheromone was identified with the (1S,2S)-aldehyde by comparing the specific rotation, enantioselective GC retention time and pheromone activity.

Cp* iridium precatalysts for selective C-h oxidation with sodium periodate as the terminal oxidant

Sodium periodate (NaIO4) is shown to be a milder and more efficient terminal oxidant for C-H oxidation with CpIr (Cp* = C 5Me5) precatalysts than ceric(IV) ammonium nitrate. Synthetically useful yields, regioselectivities, and functional group tolerance were found for methylene oxidation of substrates bearing a phenyl, ketone, ester, or sulfonate group. Oxidation of the natural products (-)-ambroxide and sclareolide proceeded selectively, and retention of configuration was seen in cis-decalin hydroxylation. At 60 C, even primary C-H bonds can be activated: whereas methane was overoxidized to CO2 in 39% yield without giving partially oxidized products, ethane was transformed into acetic acid in 25% yield based on total NaIO4. 18O labeling was demonstrated in cis-decalin hydroxylation with 18OH2 and NaIO 4. A kinetic isotope effect of 3.0 ± 0.1 was found in cyclohexane oxidation at 23 C, suggesting C-H bond cleavage as the rate-limiting step. Competition experiments between C-H and water oxidation show that C-H oxidation of sodium 4-ethylbenzene sulfonate is favored by 4 orders of magnitude. In operando time-resolved dynamic light scattering and kinetic analysis exclude the involvement of metal oxide nanoparticles and support our previously suggested homogeneous pathway.

Mild oxidative conversion of nitroalkanes into carbonyl compounds in ionic liquids

Basic hydrogen peroxide and sodium perborate were found to be cheap and efficient alternatives for the conversion of primary and secondary nitro to carbonyl compounds (Nef reaction) in ionic liquids. Copyright Taylor & Francis Group, LLC.

Nitroalkanes in Aqueous Medium as an Efficient and Eco-Friendly Source for the One-Pot Synthesis of 1,4-Diketones, 1,4-Diols, δ-Nitroalkanols, and Hydroxytetrahydrofurans

The Michael addition of primary aliphatic nitro compounds to α,β-unsaturated enones, performed in aqueous media, provides the one-pot synthesis of 1,4-diketones, 1,4-diols, δ-nitroalkanols, and hydroxytetrahydrofurans, respectively, by the appropriate cho

Electrooxidative transformation of unsubstituted and substituted nitro hydrocarbons into carbonyl compounds

Alkaline salts of aci-forms of secondary nitro compounds, viz., β-nitropropylbenzene, nitrocyclohexane, 5-nitroheptan-2-one, and methyl-4-nitrohexanoate, were selectively or predominately oxidized into the corresponding ketones and their ketals under conditions of undivided amperostatic electrolysis in methanol. Mixtures of the corresponding aldehydes, their acetals, and methyl carboxylates were formed under similar conditions from the salts of primary nitro compounds, viz., 1-nitrohexane, nitromethylbenzene, and β-nitroethylbenzene.

Unprecedented, selective Nef reaction of secondary nitroalkanes promoted by DBU under basic homogeneous conditions

Secondary nitrocompounds can be converted into the corresponding ketones under basic conditions using DBU in acetonitrile. Primary nitroalkanes are unaffected by these conditions. Elsevier Science Ltd. All rights reserved.

Transition metal-catalysed acylation of α,β-unsaturated carbonyl compounds with acylstannanes

Acylstannanes were found to add to such α,β-unsaturated carbonyl compounds as enones or ynoates in the presence of a nickel or palladium catalyst to give 2-stannyl-4-oxoalk-2-enoates or 1,4-diketones, whereas the three component coupling between acylstannanes, enones and aldehydes provided 2-hydroxymethyl 1,4-diketones.