Bindone

Bindone
Names
Preferred IUPAC name
[1,2′-Biindenylidene]-1′,3,3′(2H)-trione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.415 Edit this at Wikidata
EC Number
  • 216-956-9
UNII
  • InChI=1S/C18H10O3/c19-15-9-14(10-5-1-2-6-11(10)15)16-17(20)12-7-3-4-8-13(12)18(16)21/h1-8H,9H2
    Key: YMFDOLAAUHRURP-UHFFFAOYSA-N
  • C1C(=C2C(=O)C3=CC=CC=C3C2=O)C4=CC=CC=C4C1=O
Properties
C18H10O3
Molar mass 274.275 g·mol−1
Appearance yellow solid
Density 1.444 g/cm3[1]
Melting point 208–211 °C (406–412 °F; 481–484 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bindone is an organic compound with the formula C6H4COCH2C=C(CO)2C6H4. A yellowish solid, it is classified as an aromatic triketone.

Reactions

Bindone has been used for the detection of primary amines. It turns violet in their presence. Aromatic amines turn this reagent blue.[2]

Preparation

Bindone can be prepared by the condensation of two equivalents of 1,3-indandione. When the condensation is conducted in a solution of pyridine, triindone and other products are also observed.[3][4]

Bindone formation from two molecules of 1,3-indandione

References

  1. ^ Wilbuer, Jennifer; Schnakenburg, Gregor; Esser, Birgit (2016). "Syntheses, Structures and Optoelectronic Properties of Spiroconjugated Cyclic Ketones". European Journal of Organic Chemistry. 2016 (14): 2404–2412. doi:10.1002/ejoc.201600235.
  2. ^ Vecera, Miroslov (2012). Detection and Identification of Organic Compounds. Springer Science & Business Media. p. 319. ISBN 9781468418330.
  3. ^ Jacob, Kochurani; Sigalov, Mark; Becker, James Y.; Ellern, Arkady; Khodorkovsky, Vladimir (2000). "Self-Condensation of 1,3-Indandione: A Reinvestigation". European Journal of Organic Chemistry (11): 2047–2055. doi:10.1002/1099-0690(200006)2000:11<2047::AID-EJOC2047>3.0.CO;2-H.
  4. ^ Sharma, Lalit Kumar; Kim, Kyung Bo; Elliott, Gregory I. (2011). "A selective solvent-free self-condensation of carbonyl compounds utilizing microwave irradiation". Green Chemistry. 13 (6): 1546. doi:10.1039/c1gc15164a.
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