Bindone

Bindone
Names
	Preferred IUPAC name [1,2′-Biindenylidene]-1′,3,3′(2H)-trione
Identifiers
CAS Number	1707-95-5;
3D model (JSmol)	Interactive image;
ChemSpider	14812;
ECHA InfoCard	100.015.415
EC Number	216-956-9;
PubChem CID	15569;
UNII	INB7800050;
CompTox Dashboard (EPA)	DTXSID00168932 ;
	InChI 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;
	SMILES C1C(=C2C(=O)C3=CC=CC=C3C2=O)C4=CC=CC=C4C1=O;
Properties
Chemical formula	C18H10O3
Molar mass	274.275 g·mol−1
Appearance	yellow solid
Density	1.444 g/cm3
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). Infobox references

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]

References

^ 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.
^ Vecera, Miroslov (2012). Detection and Identification of Organic Compounds. Springer Science & Business Media. p. 319. ISBN 9781468418330.
^ 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.
^ 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.

External links

Media related to Bindone at Wikimedia Commons

[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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