1-Indanone is the organic compound with the formula C6H4(CH2)2CO. It is one of two isomeric benzocyclopentanones, the other being 2-indanone. It is a colorless solid. 1-Indanone is a substrate for the enzyme indanol dehydrogenase.

1-Indanone
Names
Preferred IUPAC name
2,3-Dihydro-1H-inden-1-one
Other names
α-Hydroindone
Identifiers
3D model (JSmol)
507957
ChEBI
ChemSpider
ECHA InfoCard 100.001.337 Edit this at Wikidata
EC Number
  • 201-470-1
142414
KEGG
UNII
  • InChI=1S/C9H8O/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4H,5-6H2
    Key: QNXSIUBBGPHDDE-UHFFFAOYSA-N
  • C1CC(=O)C2=CC=CC=C21
Properties
C9H8O
Molar mass 132.162 g·mol−1
Appearance Colorless solid
Melting point 38–42 °C (100–108 °F; 311–315 K)
Boiling point 243–245 °C (469–473 °F; 516–518 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
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).

Preparation

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It is prepared by oxidation of indane or indene.[1] It can also be prepared by cyclization of phenylpropionic acid.

 

Uses

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1-Indanone is an intermediate in the synthesis of a variety of pharmaceutical drugs including 2-aminoindane (using beta-keto-oxime formation with isoamylnitrite followed by reduction), drinidene, pirandamine,[2] and pyrophendane.

References

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  1. ^ R. A. Pacaud, C. F. H. Allen (1938). "α-Hydroindone". Org. Synth. 18: 47. doi:10.15227/orgsyn.018.0047.
  2. ^ I. Jirkovsky, L. G. Humber and R. Noureldin,Eur. J. Med. Chem., 11, 571 (1976)