2,3,4-Pentanetrione

changed Pentanetrione.svg Pentane-2,3,4-trione PentanetrioneDimethyltriketone 1S/C5H6O3/c1-3(6)5(8)4(2)7/h1-2H3 MVDYEFQVZNBPPH-UHFFFAOYSA-N correct chemspider 921-11-9 correct CAS correct FDA 84GH569GKT 136703 correct chemspider 120466 correct EBI CC(=O)C(=O)C(=O)C 5 3 6 red-orange oil 2,3,4-Triketohexane, 2,3,5-Triketohexane, 2,3,5-Triketohexane, 2,4,6-Triketoheptane triketones 2,3,4-Pentanetrione (or IUPAC name pentane-2,3,4-trione, triketopentane or dimethyl triketone) is the simplest linear triketone, a ketone with three C=O groups. It is an organic molecule with formula CH3COCOCOCH3.Townshend A. Burns D. T. Lobinski Ryszard Newman E. J. Guilbault G. Marczenko Z. Onishi H. Dictionary of Analytical Reagents 1993 CRC Press 9780412351501 766 https://books.google.com/books?id=ft4wJ6qXptcC&pg=PA766 en Production 2,3,4-Pentanetrione can be made by oxidizing 2,4-pentanedione with selenium dioxide.Arora Amit Carbohydrates And Proteins 2006 Discovery Publishing House 9788183561785 145 https://books.google.com/books?id=9bSz1ZkJ41AC&pg=PA145 en Ludwig Wolff made the 2,3 oxime by reacting hydroxylamine with isonitrosoacetylacetone in cold, aqueous, concentrated solution.Wolff Ludwig Ueber Diazoanhydride Justus Liebig's Annalen der Chemie 1902 325 2 194 10.1002/jlac.19023250202 https://zenodo.org/record/1427537 Yet other ways to make triones start from a β-dione, and oxidise the carbon at the α position, between the two ketone groups. Different methods include reaction with bromine to make a dibromide, and then reacting with acetaldehyde and hydrolysing.Dayer Francis Dao Huu L? Gold Hellmut Rod?-Gowal Heike Dahn Hans Zur Herstellung von 1,2,3-Tricarbonylverbindungen aus 1,3-Dicarbonylverbindungen. 27. Mitteilung ?ber Reduktone und Tricarbonylverbindungen [1] Helvetica Chimica Acta 6 November 1974 57 7 2201–2209 10.1002/hlca.19740570736 Nitrogen oxides can also be used. Another way is by reacting 2,4-pentandedione with p-nitroso-N,N-dimethylaniline; forming an α-diazo-β-dicarbonyl derivative compound, and then reacting that with triphenylphosphine, and then hydrolyzing with sodium nitrite solution. Or the α-diazo-β-dicarbonyl derivative can be treated with tert-butylhypochlorite. Properties 2,3,4-Pentanetrione appears as an orangy-red oil. The more intense colour is due to the greater conjugation of double bonds, and potential resonance.Panda H. Modern Technology of Textile Dyes & Pigments 2016 Niir Project Consultancy Services 9789381039717 85–86 https://books.google.com/books?id=fNNEDAAAQBAJ&pg=PR9-IA41 en 2nd Revised The type of colour centre is called a dependent chromophore, as when there are fewer C=O groups the colour is less intense or absent. So diacetyl with two carbonyls groups is yellow, and acetone with one has no colour.Sharma Dr B. K. Spectroscopy 1981 Krishna Prakashan Media 9788182830189 S-125 https://books.google.com/books?id=qYEw-OKqNCwC&pg=SL19-PA125 en At a reduced pressure of 20 mmHg it boils at 60 °C. It is hygroscopic. The odour is strong and not bad.Calvin Melvin Wood C. L. Conjugation of Carbonyl Groups and the Absorption Spectrum of Triketopentane Journal of the American Chemical Society November 1940 62 11 3152–3155 10.1021/ja01868a072 1940JAChS..62.3152C Reactions On absorbing water, perhaps from the atmosphere, 2,3,4-pentanetrione forms a hydrate. The hydrate melts at 52 °C. The hydrate with formula CH3COC(OH)2COCH3 is colourless.von Richter Victor Organic chemistry; or, Chemistry of the carbon compounds https://archive.org/details/in.ernet.dli.2015.217027 1934 73 10.1002/jctb.5000534313 2,3,4-Pentanetrione is a strong reducing agent.Arnett Edward M. Mendelsohn Morris A. Destructive Autoxidation of Metal Chelates. IV. Kinetics and Mechanism Journal of the American Chemical Society October 1962 84 20 3824–3829 10.1021/ja00879a008 1962JAChS..84.3824A Thermal decomposition catalyzed by copper sulfate results in carbon dioxide and diacetyl. 2,3,4-Pentanetrione reacts with hydrogen peroxide to yield acetic acid and carbon monoxide. Adding HOOH between C2 and C4 yields a cyclic intermediate which decomposes.Borowski Tomasz Bassan Arianna Siegbahn Per E.M. DFT study of the uncatalyzed dioxygenation of acireductone Journal of Molecular Structure: THEOCHEM October 2006 772 1–3 89–92 10.1016/j.theochem.2006.06.025 With light or organic peroxides, a free radical reaction can take place (as with triketones), whereby the molecule is slit into CH3COCO• and CH3CO• fragments. These can combine with intact molecules or each other to form other ketones.Urry W. H. Pai Mei-Shu H. Chen C. Y. Acyl Exchange Reactions of Vicinal Triones Journal of the American Chemical Society December 1964 86 23 5342–5343 10.1021/ja01077a066 1964JAChS..86.5342U When heating 2,3,4-pentanetrione with oxygen, the oxidation products are diacetyl, acetic acid, water and carbon dioxide. Alkalis convert it into acetic acid and formaldehyde. 2,3,4-Pentanetrione does a condensation reaction with o-phenylenediamine to yield methyl-quinoxaline-2-methylketone, a heterocyclic dicycle. In this the carbon number 2 and 3 react with the amine groups, leaving the CO on number 5 alone.Chesseman G. W. H. Cookson R. F. The Chemistry of Heterocyclic Compounds, Condensed Pyrazines 2009 John Wiley & Sons 9780470188859 130 https://books.google.com/books?id=9265RLc5j-8C&pg=PA130 en Another condensation can happen with 2,5,6-triamino-4(3H)pyrimidinone giving 6-acetyl-2-amino-7-methyl-4(3H)pteridinone.Brown D. J. The Chemistry of Heterocyclic Compounds, Fused Pyrimidines: Pteridines 2009 John Wiley & Sons 9780470188378 89 https://books.google.com/books?id=E7-zjIVUekUC&pg=PA89 en Grignard agents react. Phenyl magnesium bromide in excess reacting with 2,3,4-pentanetrione gives phenylacetylcarbinol and also methyldiphenylcarbinol.The Reaction of Organomagnesium Compounds With Triketones Reuben F. Miller Louisiana State University and Agricultural & Mechanical College 1952 http://digitalcommons.lsu.edu/cgi/viewcontent.cgi?article=9004&context=gradschool_disstheses Derivatives Derivatives include 2,3,4-pentanetrione-3-oxime, 2,3,4-pentanetrione-3-(O-methyloxime), 2,3,4-pentanetrione-2-oxime, 2,3,4-pentanetrione-2,3-dioxime, 2,3,4-pentanetrionetrioxime, 2,3,4-pentanetrione semicarbazone, 2,3,4-pentanetrione phenylhydrazone, 2,3,4-pentanetrione bis(phenylhydrazone). The 3-oxime melts at 75 °C and the bis(semicarbazone) has a melting point of 221 °C. References Category:Triketones Category:Conjugated ketones