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P7754 Sigma-Aldrich

Acetylacetone

ReagentPlus®, ≥99%

Synonym: 2,4-Pentanedione

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Properties

grade   ReagentPlus®
vapor density   3.5 (vs air)
vapor pressure   6 mmHg ( 20 °C)
assay   ≥99%
autoignition temp.   662 °F
expl. lim.   11.4 %
refractive index   n20/D 1.452(lit.)
bp   140.4 °C(lit.)
mp   −23 °C(lit.)
density   0.975 g/mL at 25 °C(lit.)
Gene Information   human ... ACHE(43), BCHE(590), CES1(1066)

Description

Application

Acetylacetone is used as transition-metal chelating agent.

Packaging

1 L in glass bottle

100, 500 mL in glass bottle

Packaged in glass bottles

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
21-23-24/25
RIDADR 
UN 2310 6.1(3) / PGIII
WGK Germany 
1
RTECS 
SA1925000
Flash Point(F) 
100.4 °F
Flash Point(C) 
38 °C

Protocols & Articles

Articles

Determination of Water Content in Acetylacetone Using Karl Fischer Titration

Ketones have a tendency to form ketals. At the same time water is formed. Cyclohexanone and acetone react rapidly, long chain ketones react more slowly. Aromatically substituted ketones only react ve...
Keywords: Titrations

Peer-Reviewed Papers

References

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Identifying Chelators for Metalloprotein Inhibitors Using a Fragment-Based Approach J. A. Jacobsen, et al., J. Med. Chem. 54, 591-602, (2011)

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The synthesis and photophysics of tris-heteroleptic cyclometalated iridium complexes. Edkins RM, Wriglesworth A, Fucke K, et al. Dalton Trans. 40(38), 9672-8, (2011)

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A general chelate-assisted co-assembly to metallic nanoparticles-incorporated ordered mesoporous carbon catalysts for Fischer-Tropsch synthesis. Sun Z, Sun B, Qiao M, et al. J. Am. Chem. Soc. 134(42), 17653-60, (2012)

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The three-his triad in Dke1: comparisons to the classical facial triad. Diebold AR, Neidig ML, Moran GR, et al. Biochemistry 49(32), 6945-52, (2010)

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Basic-functionalized recyclable ionic liquid catalyst: A solvent-free approach for Michael addition of 1,3-dicarbonyl compounds to nitroalkenes under ultrasound irradiation. Narayanaperumal S, da Silva RC, Feu KS, et al. Ultrason. Sonochem. 20(3), 793-8, (2013)

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Automatized flow-batch method for fluorescent determination of free glycerol in biodiesel samples using on-line extraction. Lima MB, Insausti M, Domini CE, et al. Talanta 89, 21-6, (2012)

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Use of a new hybrid sol-gel zirconia matrix in the removal of the herbicide MCPA: a sorption/degradation process. Aronne A, Sannino F, Bonavolontà SR, et al. Environ. Sci. Technol. 46(3), 1755-63, (2012)

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Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. Randy M Wadkins et al J. Med. Chem. 48, 2906-15, (2005)

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The catalytic effect of water on the keto-enol tautomerism. Pyruvate and acetylacetone: a computational challenge. Alagona G, Ghio C, and Nagy PI Phys. Chem. Chem. Phys. 12(35), 10173-88, (2010)

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Direct and highly regioselective and enantioselective allylation of β-diketones Chalifoux, W. A.; Reznik, S. K.; Leighton, J. L. Nature 487, 86-89, (2012)

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Synthesis and characterization of Fe(II) β-diketonato complexes with relevance to acetylacetone dioxygenase: insights into the electronic properties of the 3-histidine facial triad. Park H, Baus JS, Lindeman SV, et al. Inorg. Chem. 50(23), 11978-89, (2011)

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Probing autoinducer-2 based quorum sensing: the biological consequences of molecules unable to traverse equilibrium states. Tsuchikama K, Lowery CA, and Janda KD J. Org. Chem. 76(17), 6981-9, (2011)

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Enzyme catalytic promiscuity: The papain-catalyzed Knoevenagel reaction. Hu W, Guan Z, Deng X, et al. Biochimie 94(3), 656-61, (2012)

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DFT modeling, UV-Vis and IR spectroscopic study of acetylacetone-modified zirconia sol-gel materials. Georgieva I, Danchova N, Gutzov S, et al. J. Mol. Model. 18(6), 2409-22, (2012)

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Dke1--structure, dynamics, and function: a theoretical and experimental study elucidating the role of the binding site shape and the hydrogen-bonding network in catalysis. Brkić H, Buongiorno D, Ramek M, et al. J. Biol. Inorg. Chem. 17(5), 801-15, (2012)

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Photochemistry of acetylacetone isolated in parahydrogen matrices upon 266 nm irradiation. Lozada-García RR, Ceponkus J, Chevalier M, et al. Phys. Chem. Chem. Phys. 14(10), 3450-9, (2012)

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Mechanisms of the Knoevenagel hetero Diels-Alder sequence in multicomponent reactions to dihydropyrans: experimental and theoretical investigations into the role of water. Frapper G, Bachmann C, Gu Y, et al. Phys. Chem. Chem. Phys. 13(2), 628-36, (2011)

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Fe(II) complexes that mimic the active site structure of acetylacetone dioxygenase: O2 and NO reactivity. Park H, Bittner MM, Baus JS, et al. Inorg. Chem. 51(19), 10279-89, (2012)

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Spectroscopic studies and antibacterial activities of some new 16-membered octaazamacrocyclic complexes derived from thiocarbohydrazide and pentane-2,4-dione. Singh DP, Kumar K, and Mehani ne'e Chopra R Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 78(2), 629-34, (2011)

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Supramolecular structure and spectral studies on mixed-ligand complexes derived from β-diketone with azodye rhodanine derivatives. El-Sonbati AZ, Diab MA, Belal AA, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 99, 353-60, (2012)

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Identification of human fumarylacetoacetate hydrolase domain-containing protein 1 (FAHD1) as a novel mitochondrial acylpyruvase. Pircher, H., et al. J. Biol. Chem. 286, 36500-8, (2011)

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Trace level determination of beryllium in natural and flavored mineral waters after pre-concentration using activated carbon. Kılınç E, Bakırdere S, and Yaman M Food Addit. Contam. Part A. Chem. Anal. Control. Expo. Risk Assess. 28(4), 455-60, (2011)

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Microwave promoted C6-alkylation of purines through S(N)Ar-based reaction of 6-chloropurines with 3-alkyl-acetylacetone. Guo HM, Zhang Y, Niu HY, et al. Org. Biomol. Chem. 9(7), 2065-8, (2011)

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Nano-sized, quaternary titanium(IV) metal-organic frameworks with multidentate ligands. Baranwal BP and Singh AK Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 77(5), 938-41, (2010)

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A facile synthesis of new monoazo disperse dyes derived from 4-hydroxyphenylazopyrazole-5-amines: evaluation of microwave assisted dyeing behavior. Al-Etaibi AM, El-Apasery MA, Ibrahim MR, et al. Molecules 17(12), 13891-909, (2012)

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New tetradentate Schiff bases of 2,2-dimethyl-1,3-diaminopropane and acetylacetone derivatives and their vanadyl complexes. Mohammadi K and Rastegari M Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 97, 711-6, (2012)

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Sensitive fluorescence detection of etimicin based on derivatives of formaldehyde and acetylacetone. Zhuang Y and Cao L J. Fluoresc. 23(1), 1-5, (2013)

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Sensitive and simple flow injection analysis of formaldehyde using an activated barrel plating nickel electrode. Chen PY, Yangi HH, Zen JM, et al. J. AOAC Int. 94(5), 1585-91, (2011)

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Validated spectrofluorimetric method for determination of sulpiride in commercial formulations using Hantzsch condensation reaction. Shah J, Jan MR, Khan MN, et al. Pak. J. Pharm. Sci. 26(5), 921-8, (2013)

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Merck 14,81

Beil. 1,IV,3662

Fieser 1,10

Aldrich MSDS 1, 1436:D / Corp MSDS 1 (2), 2712:D / FT-IR 2 (1), 667:B / FT-IR 1 (1), 425:A / FT-NMR 1 (1), 661:B / IR-Spectra (3), 252:C / IR-Spectra (2), 225:H / NMR-Reference 2 (1), 388:B / RegBook 1 (1), 465:G / Sax 6, 100 / Sigma FT-IR 1 (2), 237:B / Structure Index 1, 66:E:4 / Vapor Phase 3, 511:B

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