1,3-Indandione

changed 477205481 1,3-indanon.svg skin-invert-image 130px Skeletal formula Indandione-3D-balls.png 160 Ball-and-stick model 1H-Indene-1,3(2H)-dione Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione correct chemspider 11322 1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2 O=C2c1ccccc1C(=O)C2 UHKAJLSKXBADFT-UHFFFAOYAR correct EBI 283521 78877 correct chemspider 1S/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2 correct chemspider UHKAJLSKXBADFT-UHFFFAOYSA-N correct CAS 606-23-5 correct FDA 4DJN7YG35G 11815 C1C(=O)C2=CC=CC=C2C1=O 9 6 2 white solid 1.37 g/cm3 129 to 132 1,3-Indandione at Sigma-AldrichMSDS at Acros Organics, retrieved on June 16, 2011 slight 1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C6H4(CO)2CH2. It is a β-diketone with indane as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowishru Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490. or even green. It is a popular chemical scaffold (building block of various useful chemical compounds),Asadi Shima Mohammadi Ziarani Ghodsi The molecular diversity scope of 1,3-indandione in organic synthesis Molecular Diversity 2016 20 1 111–152 10.1007/s11030-015-9589-z 25957619 10.1016/j.eurpolymj.2020.110178 Recent advances on visible light photoinitiators of polymerization based on Indane-1,3-dione and related derivatives 2021 Dumur Frédéric European Polymer Journal 143 110178 2021EurPJ.14310178D 229445473 free and derivatives antagonize Vitamin K receptors.10.2174/1389557518666180330101809 Indandione and Its Derivatives - Chemical Compounds with High Biological Potential 2018 Pluskota Robert Koba Marcin Mini-Reviews in Medicinal Chemistry 18 15 1321–1330 29600759 4516564 Structural properties Solid 1,3-indandione is a diketone, As a solution in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This acid-base behavior explains many properties of the compound.October 2023 Preparation thumb|Route to indandione|left 1,3-Indandione was first obtained by Claisen condensation of ethyl acetate and dimethyl phthalate.Wislicenus Wilhelm Ueber die Vereinigung verschiedener Ester durch Natrium Berichte der Deutschen Chemischen Gesellschaft 1887 20 589–595 10.1002/cber.188702001137 A related route entails the reaction of benzoyl chloride with malonyl dichloride. It also can be obtained by oxidation of indane. Chemical properties thumb|Route to bi- and triindone|320px|left The structure of the title compound has been confirmed by X-ray crystallography.Chetkina L. A. Belsky V. K. X-Ray structure investigation of 1,3-indandione and 1,3-dicyanomethyleneindan derivatives: A review Crystallography Reports 2008 53 4 579–607 10.1134/S1063774508040081 2008CryRp..53..579C Unlike some other 1,3-diketones, it does not crystallize as the enol. The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation easily, resulting in bi- and triindone. Bromination occurs at the 2-position: C6H4(CO)2CH2 + 2 Br2 -> C6H4(CO)2CBr2 + 2HBr One or both carbonyl groups can be reduced to alcohol groups or methylene groups, depending on the method used. C6H4(CO)2CH2 + H2 -> C6H4(CHOH)(CO)CH2 C6H4(CO)(CHOH)CH2 + H2 -> C6H4(CHOH)2CH2 C6H4(CO)2CH2 + 4 H2 -> C6H4(CH2)2CH2 + 2 H2O Uses thumb|left|Diphenadione a commercial rodenticide derived from 1,3-indandione|130px 1,3-Indandiones with a substituent at the 2-position are potent rodenticides. Commercial products include pindone, chlorophacinone, and diphenadione. These compounds function as vitamin K antagonists, inducing hemorrhage in the affected animals.Buckle Alan Ullmann's Encyclopedia of Industrial Chemistry Rodenticides 2000 10.1002/14356007.a23_211 3-527-30673-0 References External links