2,4-Dimethyl-3-pentanone

Base Information

• Chemical Name: 2,4-Dimethyl-3-pentanone
• CAS No.: 565-80-0
• Molecular Formula: C7H14O
• Molecular Weight: 114.188
• Hs Code.: 2914.19 Oral rat LD50: 3536 mg/kg
• European Community (EC) Number: 209-294-7
• NSC Number: 14662
• UNII: 7AAP3A50IG
• DSSTox Substance ID: DTXSID3038771
• Nikkaji Number: J6.514E
• Wikidata: Q27159900
• Metabolomics Workbench ID: 44873
• ChEMBL ID: CHEMBL3560924
• Mol file: 565-80-0.mol

Synonyms:2,4-DIMETHYL-3-PENTANONE;565-80-0;Diisopropyl ketone;2,4-Dimethylpentan-3-one;Isobutyrone;Isopropyl ketone;3-Pentanone, 2,4-dimethyl-;DIISOPROPYLKETONE;2,4-dimethyl-pentan-3-one;EINECS 209-294-7;NSC 14662;(iso-C3H7)2CO;UNII-7AAP3A50IG;PM 2763;7AAP3A50IG;DTXSID3038771;3-PENTANONE,2,4-DIMETHYL;NSC-14662;MFCD00008918;isopropylketone;diisopropylketon;di-iso-propyl ketone;3-Pentanone,4-dimethyl-;SCHEMBL25173;2, 4-Dimethyl-3-pentanone;Dimethyl-3-pentanone, 2,4-;CHEMBL3560924;DTXCID1018771;CHEBI:87754;2,4-Dimethyl-3-pentanone, 98%;NSC14662;Tox21_303876;AKOS005206866;NCGC00357269-01;CAS-565-80-0;LS-101945;D0770;FT-0610158;EN300-67377;2,4-Dimethyl-3-pentanone (diisopropyl ketone);A831104;Q27159900

Chemical Property of 2,4-Dimethyl-3-pentanone

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 11mmHg at 25°C
• Melting Point: -80 °C
• Refractive Index: 1.3999
• Boiling Point: 127.7 °C at 760 mmHg
• Flash Point: 22.1 °C
• PSA: 17.07000
• Density: 0.804 g/cm³
• LogP: 1.86750
• Storage Temp.: Flammables area
• Water Solubility.: insoluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 114.104465066
• Heavy Atom Count: 8
• Complexity: 72.4

Purity/Quality:

99.9% ^*data from raw suppliers

Isobutyrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn
• Hazard Codes: F,Xn
• Statements: 11-20-2017/11/20
• Safety Statements: 9-16-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CC(C)C(=O)C(C)C
• Uses: DiPK has been used in automotive assembly plants as a ketonic solvent for fuel injectors and as a photoinitiator for IV-curable acrylic coatings in optical fiber gratings. The U.S. production ofDnPK was estimated to be,500,000 lb in 2005 according to the 2006 U.S. EPA Inventory Update Reporting database. 2,4-Dimethyl-3-pentanone is used in an experimental method to measure the equilibrium isotopic fractionation factor (αeq ) for C-bound H positions adjacent to carbonyl group in ketones.It is a carbonyl compound used in an experimental method to measure the equilibrium isotopic fractionation factor (αeq ) for C-bound H positions adjacent to carbonyl group in ketones. Isobutyrone is a very useful synthetic intermediate. It is an intermediate used to prepare α-aryl ketones. It is also used in Grignard reactions. 2,4-Dimethyl-3-pentanone was used in an experimental method to measure the equilibrium isotopic fractionation factor (αeq ) for C-bound H positions adjacent to carbonyl group in ketones.

Technology Process of 2,4-Dimethyl-3-pentanone

There total 196 articles about 2,4-Dimethyl-3-pentanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

2-(1'-Hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2,4-dimethylpentan-3-one (126889-57-4) → benzocyclobutenone (3469-06-5) + 2,4-dimethylpentan-3-one (565-80-0)

Guidance literature:

at 180 ℃; for 1h; under 0.5 Torr;

Reference yield: 60.0%

butanone (78-93-3) + methyl trifluoromethanesulfonate (333-27-7) → ethyl isopropyl ketone (565-69-5) + 2,2-dimethyl-3-pentanone (564-04-5) + 2,4-dimethylpentan-3-one (565-80-0)

Guidance literature:

With n-butyllithium; potassium hydride; In diethyl ether;

DOI:10.1021/jo00080a042

Reference yield: 40.4%

acetic acid (64-19-7,77671-22-8) + isobutyric Acid (79-31-2) → 3-methyl-butan-2-one (563-80-4) + acetone (67-64-1) + 2,4-dimethylpentan-3-one (565-80-0)

Guidance literature:

alumina; KOH; titania; mixture of, soaked, dried; In water; at 450 - 500 ℃; Product distribution / selectivity;

upstream raw materials:

3-isopropyl-2,2-dimethyl-oxirane

2,2,4,4-tetramethyl-1,3-cyclobutanedione

diethyl ether

methylmagnesium bromide

Downstream raw materials:

5-hydroxy-2,4,4-trimethyl-5-phenyl-3-pentanone

2-isopropyl-3-methyl-1-phenyl-2-butanol

2,4-dimethylpent-3-ylamine

3-isopropyl-2-methyl-hexan-3-ol

Refernces

Improved addition of phenyllithium to hindered ketones by the use of non-polar media

10.1016/S0040-4039(02)00597-X

The research focuses on the improved addition of phenyllithium (PhLi) to hindered ketones using non-polar media at room temperature. The study was conducted on six hindered ketones: (?)-fenchone, (?)-menthone, (+)-camphor, 3,3,5-trimethylcyclohexanone, 3,3,5,5-tetramethylcyclohexanone, and 2,4-dimethylpentan-3-one. The researchers aimed to enhance the low reactivity of these ketones towards PhLi, which traditionally yields modest results when performed in ethers like diethyl ether or THF. The experiments involved dissolving the ketones in a non-polar solvent, such as toluene or a toluene-diethyl ether mixture, and then slowly adding commercial PhLi via syringe. The mixtures were stirred at room temperature for 2 to 4 hours. The results showed significant improvements in yield compared to traditional methods, with the addition occurring in a stereospecific manner, favoring the less-hindered side. The configuration of the adducts was established using 13C NMR according to literature methods. This approach was found to be more efficient, cost-effective, and easier, offering a significant advantage for the synthesis of chiral inducers.

Rhodium-Catalyzed Cross-Coupling of Vinylarenes with Arylaluminum Reagents in the Presence of Ketones

10.1002/ejoc.201301757

The study presents a rhodium-catalyzed cross-coupling reaction between vinylarenes and arylaluminum reagents, which results in the formation of stilbene derivatives, π-conjugated organic materials of interest in organic synthesis. Key chemicals used include diethyl(phenyl)aluminum as the arylaluminum reagent, styrene as a representative vinylarene, and various ketones such as diisopropyl ketone, acetone, and pinacolone, which serve as additives that promote the reaction. The study also explores the use of different rhodium catalysts, including [RhCl(cod)]2, [Rh(OH)(cod)]2, and [Rh(OMe)(cod)]2, to optimize the reaction conditions and yield of stilbene products. The purpose of these chemicals is to facilitate an addition/elimination-type reaction that expands the scope of organic synthesis using organoaluminum reagents, which are known for their functional-group tolerance compared to other nucleophiles like organomagnesium and organolithium reagents.