Indane-1,2,3-trione

Last updated
Indane-1,2,3-trione
Indantrione.svg
Names
IUPAC name
Indane-1,2,3-trione
Other names
Indanetrione
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 213-340-1
PubChem CID
  • InChI=1S/C9H4O3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4H
    Key: WVZWEMOFSIEEMU-UHFFFAOYSA-N
  • O=C2c1ccccc1C(=O)C2=O
Properties
C9H4O3
Molar mass 160.128 g·mol−1
Appearanceraspberry-red crystals
Density 1.482 g/cm3
Boiling point 338.4 °C (641.1 °F; 611.5 K)
Reacts with water yielding ninhydrin; soluble in hot o-dichlorobenzene; slightly soluble in dichloromethane forming green solutions.
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indane-1,2,3-trione is the organic compound with the formula C6H4(CO)3. The compound is the dehydrated derivative of C6H4(CO)2C(OH)2, known as ninhydrin, which is used to reveal fingerprints.

Indane-1,2,3-trione, which reacts readily with nucleophiles (including water). Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups. [2]

To generate the ninhydrin chromophore (2-(1,3-dioxoindan-2-yl)iminoindane-1,3-dione), the amine must condense to give a Schiff base. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, generally being yellow–orange. [3]

References

  1. ↑ "Indan-1,2,3-trione". pubchem.ncbi.nlm.nih.gov. Retrieved 4 February 2022.
  2. ↑ Informatics, NIST Office of Data and. "Indan-1,2,3-trione". webbook.nist.gov. Retrieved 2025-05-08.
  3. ↑ Gill, G. Bryon; Idris, Muhammad S. Hj; Kirollos, Kirollos S. (1992-01-01). "Ene reactions of indane-1,2,3-trione (a super-enophile) and related vicinal tricarbonyl systems" . Journal of the Chemical Society, Perkin Transactions 1 (18): 2355–2365. doi:10.1039/P19920002355. ISSN   1364-5463.
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