815-57-6

Basic information

• Product Name: 3-METHYL-2,4-PENTANEDIONE
• Synonyms: 3-METHYL-2,4-PENTANEDIONE;3-METHYLPENTANE-2,4-DIONE;3-ACETYLBUTAN-2-ONE;3-ACETYL-2-BUTANONE;1,1-DIACETYLETHANE;METHYLACETYLACETONE;3-methyl-2,4-pentanedione,mixtureoftautomers;3-Methyl-2,4-Pentanedione,>95%
• CAS NO: 815-57-6
• Molecular Formula: C6H10O2
• Molecular Weight: 114.14
• EINECS: 212-420-3
• Product Categories: Miscellaneous;Environmentally-friendly Oxidation;Ligands (Environmentally-friendly Oxidation);Synthetic Organic Chemistry;C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 815-57-6.mol
• Article Data: 46

Chemical Properties

• Melting Point: -7.75°C (estimate)
• Boiling Point: 172-174 °C(lit.)
• Flash Point: 134 °F
• Appearance: clear colourless to yellow liquid
• Density: 0.981 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0638mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: 0-10°C
• PKA: pK1:10.87 (25°C)
• Water Solubility: Soluble in water.
• BRN: 635909
• CAS DataBase Reference: 3-METHYL-2,4-PENTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-2,4-PENTANEDIONE(815-57-6)
• EPA Substance Registry System: 3-METHYL-2,4-PENTANEDIONE(815-57-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 815-57-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to yellow liquid

Uses

3-Methyl-2,4-pentanedione involves in asymmetric substitution of 1,3-diphenyl-2-propenyl acetate catalyzed by amphiphilic resin-supported monodentate phosphine ligands can occur.

Synthesis Reference(s)

Chemistry Letters, 8, p. 45, 1979Journal of the American Chemical Society, 90, p. 2421, 1968 DOI: 10.1021/ja01011a039Organic Syntheses, Coll. Vol. 5, p. 785, 1973

General Description

Peroxynitrite promoted aerobic oxidation of 3-methyl-2,4-pentanedione has been reported. The kinetics of the reaction of OH radicals with 3-methyl-2,4-pentanedione has been investigated in the gas-phase using a pulsed laser photolysis-laser induced fluorescence technique. 3-methyl-2,4-pentanedione participates in asymmetric substitution of 1,3-diphenyl-2-propenyl acetate catalyzed by amphiphilic resin-supported monodentate phosphine ligands.

InChI:InChI=1/C6H10O2/c1-4(5(2)7)6(3)8/h7H,1-3H3/b5-4-

Upstream product

• 53496-45-0 4-hydroxy-3-methyl-pentan-2-one 
• 6203-88-9 2-acetoxy-2-butene 
• 7637-07-2 boron trifluoride 
• 108-24-7 acetic anhydride 
• 74-83-9 methyl bromide 
• 123-54-6 acetylacetone 
• 565-62-8 3-methylpent-3-en-2-one 
• 112-55-0 1-dodecylthiol 
• 96-14-0 3-methylpentane 
• 614-45-9 tert-Butyl peroxybenzoate 
• 1522-20-9 acetylacetone 
• 74-88-4 methyl iodide 
• 1118-66-7 4-amino-3-penten-2-one 
• 141-78-6 ethyl acetate 

Downstream Products

• 69687-79-2 1H-pyrrole, 2-ethyl-3,4,5-trimethyl- 
• 626606-73-3 3-methyl-3-(bis(4-dimethylaminophenyl)methyl)penta-2,4-dione 
• 10252-60-5 1-(4-nitrophenyl)-3,4,5-trimethylpyrazole 
• 54568-11-5 4,5,6-trimethylpyrimidin-2-ylamine 
• 5433-64-7 sulfanilic acid-(4,5,6-trimethyl-pyrimidin-2-ylamide) 
• 6050-55-1 3-(2-methyl-[1,3]oxathiolan-2-yl)-butan-2-one 
• 5683-44-3 3-methyl-2,4-pentanediol 
• 53496-45-0 4-hydroxy-3-methyl-pentan-2-one 
• 4707-47-5 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester 
• 34916-51-3 sodium enolate of 3-methylpentane-2,4-dione 
• 116660-75-4 (3R,4S)-(+)-3-methyl-4-hydroxypentan-2-one 
• 565-79-7 (3R,4R)-4-Hydroxy-3-methyl-pentan-2-one 
• 115936-19-1 (3S,4S)-(+)-3-methyl-4-hydroxypentan-2-one 
• 942126-58-1 (R)-3-acetyl-3-methyl-4,6-diphenylhex-5-en-2-one 

Relevant articles and documents

Ag-Catalyzed Insertion of Alkynyl Carbenes into C-C Bonds of β-Ketocarbonyls: A Formal C(sp2) Insertion

Here we report a silver-catalyzed alkynyl carbene insertion into β-ketocarbonyls using alkynyl N-nosylhydrazones as alkynyl carbene precursors, which provides access to trisubstituted allenyl ketones. This reaction represents the first example of an alkynyl carbene insertion into a C-C σ bond, affording products homologated with an sp2 carbon center. The products are useful substrates for further transformations. Experimental investigations and theoretical calculations suggest the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.

Synthesis and Thermal Behavior of Heteroleptic γ-Substituted Acetylacetonate-Alkoxides of Titanium

A series of heteroleptic titanium derivatives of general formula [Ti(OiPr)2(R-acac)2] with acetylacetonate ligands modified in the internal (γ- or 3-) position by different substituents (R=OAc, NO2, Me, Et, Cl, Br) has been synthesized and completely characterized by liquid multinuclear NMR and FTIR. The influence of the nature of the group on the thermal stability of the different complexes was studied by thermogravimetric analysis (TGA) and gave the following decreasing stability ranking: H22°-acac radical, which triggers the decomposition.

Scalable Synthesis of Esp and Rhodium(II) Carboxylates from Acetylacetone and RhCl3· xH2O

Rhodium(II) carboxylates are privileged catalysts for the most challenging carbene-, nitrene-, and oxo-transfer reactions. In this work, we address the strategic challenges of current organic and inorganic synthesis methods to access these rhodium(II) complexes through an oxidative rearrangement strategy and a reductive ligation reaction. These studies illustrate the multiple benefits of oxidative rearrangement in the process-scale synthesis of congested carboxylates over nitrile anion alkylation reactions, and the impressive effect of inorganic additives in the reductive ligation of rhodium(III) salts.