504-20-1 Usage
Description
2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE, also known as Diisopropylidene Acetone, is an organic compound with the chemical formula C11H20O. It is a colorless liquid with a pungent odor and is soluble in organic solvents. 2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE is characterized by its conjugated diene system and a ketone functional group, which makes it a versatile building block in organic synthesis.
Uses
Used in Pharmaceutical Industry:
2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE is used as a reagent for the preparation of biaryls by Suzuki-Miyaura cross-coupling reaction. Biaryls are important structural motifs found in many pharmaceuticals and agrochemicals, and their synthesis is crucial for the development of new drugs and active compounds.
Used in Organic Synthesis:
2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE is used as a building block in the synthesis of various organic compounds, including natural products, pharmaceuticals, and agrochemicals. Its conjugated diene system and ketone functional group make it a valuable intermediate for the preparation of complex organic molecules.
Used in Material Science:
2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE can be used as a monomer in the synthesis of polymers and materials with specific properties. Its conjugated diene system can be polymerized to form polymers with unique optical, electronic, or mechanical properties, which can be used in various applications, such as sensors, solar cells, or advanced materials.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Ketones, such as 2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Safety Profile
Moderately toxic by subcutaneous route. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ISOPHORON
Purification Methods
Crystallise phorone repeatedly from EtOH. [Beilstein 1 IV 3564.]
Check Digit Verification of cas no
The CAS Registry Mumber 504-20-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 4 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 504-20:
(5*5)+(4*0)+(3*4)+(2*2)+(1*0)=41
41 % 10 = 1
So 504-20-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3
504-20-1Relevant articles and documents
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King,Lionetti
, p. 2248 (1945)
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Clibbens,Francis
, p. 2358 (1912)
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In-situ IR Spectroscopy Study of Reactions of C3 Oxygenates on Heteroatom (Sn, Mo, and W) doped BEA Zeolites and the Effect of Co-adsorbed Water
Najmi, Sean,So, Jungseob,Stavitski, Eli,McDermott, William P.,Lyu, Yimeng,Burt, Sam P.,Hermans, Ive,Sholl, David S.,Sievers, Carsten
, p. 445 - 458 (2020/12/01)
The reactions of acetone and hydroxyacetone over heteroatom doped BEA zeolites (Sn, Mo, and W) in the presence and absence of H2O vapor are investigated using infrared spectroscopy. Acetone is converted to mesityl oxide over Sn-BEA exclusively. At higher temperatures, larger oxygenates such as phorones, aromatics, and coke form. The presence of co-adsorbed water in Sn-BEA suppresses tautomerization. H2O vapor is also beneficial for minimizing coke formation at high temperatures. Hydroxyacetone is converted into 2-hydroxypropanal over Sn-BEA, exhibiting high affinity to Sn sites up to 400 °C. Sn-BEA catalyzes conversion of hydroxyacetone into the enol in the absence of H2O, but exposure to H2O induces the formation of 2-hydroxypropanal and subsequent conversion to acrolein. The Lewis acid descriptors are used to rationalize the reaction pathways. For the isomerization of hydroxyacetone into 2-hydroxypropanal, the hardness of acid sites influences the reaction and correlates with the overall Lewis acidity of the catalysts, respectively. However, the size of the exchanged metal significantly affects aldol condensation, where keto and enol forms of acetone adsorb to active sites simultaneously.
Aldol Condensation Versus Superbase-Catalyzed Addition of Ketones to Acetylenes: A Quantum-Chemical and Experimental Study
Orel, Vladimir B.,Vitkovskaya, Nadezhda M.,Bobkov, Alexander S.,Semenova, Nadezhda V.,Schmidt, Elena Yu.,Trofimov, Boris A.
, p. 7439 - 7449 (2021/06/21)
The mechanism of aldol condensation of ketones in KOH/DMSO superbasic media has been investigated using the B2PLYP(D2)/6-311+G**//B3LYP/6-31+G? quantum-chemical approach. It is found that the interaction of three ketone molecules resulting in the formation of the cyclohex-2-enone structure [isophorone or 3,5-dicyclohexyl-5-methylspiro(5.5)undec-2-en-1-one] is thermodynamically more favorable than the interaction of two, three, or four molecules of ketone, resulting in the formation of linear products of the condensation. The formation of the condensation products with the isophorone skeleton can significantly hinder the cascade reactions of ketones with acetylenes [to afford 6,8-dioxabicyclo(3.2.1)octanes or acylcyclopentenols] promoted by superbases. In particular, the kinetically more preferable reactions of autovinylation of 2-methyl-3-butyn-2-ol and autocondensation of acetone are the reasons why interaction of acetone with acetylene does not lead to the products of the cascade assemblies. The predominant formation of the products of these side reactions is confirmed experimentally.