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Acetylacetone information


Acetylacetone
Skeletal structures of both tautomers
Ball-and-stick model of the enol tautomer
Ball-and-stick model of the enol tautomer
Ball-and-stick model of the keto tautomer
Ball-and-stick model of the keto tautomer
Space-filling model of the enol tautomer
Space-filling model of the enol tautomer
Space-filling model of the keto tautomer
Space-filling model of the keto tautomer
Names
IUPAC names
(3Z)-4-Hydroxy-3-penten-2-one (enol form)
Pentane-2,4-dione (keto form)
Other names
  • Hacac
  • 2,4-Pentanedione
Identifiers
CAS Number
  • 123-54-6 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
  • Enol form: Interactive image
Beilstein Reference
741937
ChEBI
  • CHEBI:14750 checkY
ChEMBL
  • ChEMBL191625 checkY
ChemSpider
  • 29001 checkY
ECHA InfoCard 100.004.214 Edit this at Wikidata
EC Number
  • 204-634-0
Gmelin Reference
2537
KEGG
  • C15499 checkY
PubChem CID
  • 31261
RTECS number
  • SA1925000
UNII
  • 46R950BP4J checkY
UN number 2310
CompTox Dashboard (EPA)
  • DTXSID4021979 Edit this at Wikidata
InChI
  • InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3 checkY
    Key: YRKCREAYFQTBPV-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
    Key: YRKCREAYFQTBPV-UHFFFAOYAO
SMILES
  • O=C(C)CC(=O)C
  • CC(=O)CC(=O)C
  • Enol form: CC(O)=CC(=O)C
Properties
Chemical formula
C5H8O2
Molar mass 100.117 g·mol−1
Appearance Colorless liquid
Density 0.975 g/mL[1]
Melting point −23 °C (−9 °F; 250 K)
Boiling point 140 °C (284 °F; 413 K)
Solubility in water
16 g/(100 mL)
Magnetic susceptibility (χ)
−54.88·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H226, H302, H311, H320, H331, H335, H341, H370, H412
Precautionary statements
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P311, P312, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 34 °C (93 °F; 307 K)
Autoignition
temperature
340 °C (644 °F; 613 K)
Explosive limits 2.4–11.6%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acetylacetone is an organic compound with the chemical formula CH3−C(=O)−CH2−C(=O)−CH3. It is classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3−C(=O)−CH=C(−OH)−CH3. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications.[2] Acetylacetone is a building block for the synthesis of many coordination complexes as well as heterocyclic compounds.

  1. ^ "05581: Acetylacetone". Sigma-Aldrich.
  2. ^ Thomas M. Harris (2001). "2,4-Pentanedione". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp030. ISBN 0471936235.

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Acetylacetone

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Acetylacetone is an organic compound with the chemical formula CH3−C(=O)−CH2−C(=O)−CH3. It is classified as a 1,3-diketone. It exists in equilibrium with...

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Enol

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acetaldehyde (K = [enol]/[keto] ≈ 3×10−7). In 1,3-diketones, such as acetylacetone (2,4-pentanedione), the enol form is favored. The acid-catalyzed conversion...

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Vanadyl acetylacetonate

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compound with the formula VO(acac)2, where acac– is the conjugate base of acetylacetone. It is a blue-green solid that dissolves in polar organic solvents....

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Tautomer

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Keto-enol tautomerization typically strongly favors the keto tautomer, but an important exception is the case of 1,3-diketones such as acetylacetone....

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Pentanedione

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Pentanedione may refer to: Acetylacetone (2,4-pentanedione) Acetylpropionyl (2,3-pentanedione) C5H8O2 Cyclopentanedione This set index article lists chemical...

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Hydrogen bond

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NMR spectrum. For example, the acidic proton in the enol tautomer of acetylacetone appears at δ H {\displaystyle \delta _{\text{H}}}  15.5, which is about...

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Ethyl acetoacetate

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LiCH2C(O)CH(Na)CO2Et + RX → RCH2C(O)CH(Na)CO2Et + LiX Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand...

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Ketone

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diacetyl (CH3C(O)C(O)CH3), once used as butter-flavoring in popcorn. Acetylacetone (pentane-2,4-dione) is virtually a misnomer (inappropriate name) because...

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Sodium acetylacetonate

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water-soluble solid is the conjugate base of acetylacetone. The compound is prepared by deprotonation of acetylacetone: NaOH + CH2(C(O)CH3)2 → NaCH(C(O)CH3)2...

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Acetylation

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030.0001. Denoon, C. E. Jr.; Adkins, Homer; Rainey, James L. (1940). "Acetylacetone". Organic Syntheses. 20: 6. doi:10.15227/orgsyn.020.0006. Arpe, Hans-Jürgen...

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Dicarbonyl

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acetylacetone, CH3C(O)CH2C(O)CH3. Dimedone is a cyclic 1,3-diketone. 1,3-Indandione is the cyclic 1,3-diketone fused to a benzene ring. Acetylacetone...

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Isopropenyl acetate

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colorless liquid is significant commercially as the principal precursor to acetylacetone. In organic synthesis, it is used to prepare enol acetates of ketones...

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C5H8O2

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The molecular formula C5H8O2 may refer to: Acetylacetone Acetylpropionyl Allyl acetate Angelic acid Coffee furanone Cyclobutanecarboxylic acid Ethyl acrylate...

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Aluminium acetylacetonate

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complex with formula Al(C5H7O2)3. This aluminium complex with three acetylacetone ligands is used in research on Al-containing materials. The molecule...

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Metal acetylacetonates

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metal salt with acetylacetone, acacH: Mz+ + z Hacac ⇌ M(acac)z + z H+ Addition of base assists the removal of a proton from acetylacetone and shifts the...

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Acetamide

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Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination. It can also be...

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Hexafluoroacetylacetone

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enol CF3C(OH)=CHC(O)CF3. For comparison under the same conditions, acetylacetone is 85% enol. Metal complexes of the conjugate base exhibit enhanced...

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Methylene bridge

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of compounds which contain methylene bridges include: Malonic acid Acetylacetone Malononitrile Methyl group Methylene group Methyne W. A. Herrmann (1982)...

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Titanium tetrachloride

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results from treatment of titanium tetrachloride with excess acetylacetone: TiCl4 + 2 Hacac → Ti(acac)2Cl2 + 2 HCl Organic amines react with TiCl4...

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Polydioxanone

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process requires heat and an organometallic catalyst like zirconium acetylacetone or zinc L-lactate. It is characterized by a glass transition temperature...

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Scandium acetylacetonate

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molecular geometry. It was first prepared by treating scandium nitrate with acetylacetone in the presence of ammonia. Anderson, Thomas J.; Neuman, Melvin A.;...

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Tetraacetylethane

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NaCH(C(O)CH3)2 → [CH(C(O)CH3)2]2 + 2 NaI Reminiscent of the case of acetylacetone, tetraacetylethane exists as the enol, as established by X-ray crystallography...

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Chelation

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"CLXII.—Researches on residual affinity and co-ordination. Part II. Acetylacetones of selenium and tellurium". Journal of the Chemical Society, Transactions...

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Pyrazole

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of 1,3-diketones with hydrazine (Knorr-type reactions). For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole: CH3C(O)CH2C(O)CH3   +   N2H4...

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