4939. Indene

Nomenclature

CAS number: 95-13-6
Indonaphthene.
C9H8; mol wt 116.16.
C 93.06%, H 6.94%.

Description and references

Found in the tars from coal, lignite, and crude petr. Isoln from coal tar: Weissgerber, Ber. 42, 569 (1909); Brennst.-Chem. 5, 208 (1924); Weissgerber, Seidler, Ber. 60, 2088 (1927). Prepn from acetylene over activated charcoal at 625°: Zelinsky, Ber. 57, 264 (1924). Manuf from tetrahydronaphthalene by passing over SiO2-Al2O3 catalyst at 670°: GB 578083 (1946). Prepn from o-BrCH2C6H4CH2CH2Br and triphenylphosphine: Bestmann et al., Ann. 718, 33 (1968).

Chemical structure

Properties

Liquid. d44 1.0081; d420 0.9968; d450 0.9692. mp 1.8°. bp760 181.6°; bp400 157.8°; bp200 135.6°; bp100 114.7°; bp60 100.8°; bp40 90.7°; bp20 73.9°; bp10 58.5°; bp5 44.3°; bp1.0 16.4°. nD18.5 1.5773. Absorption spectrum: Morton, de Gouveia, J. Chem. Soc. 1934, 911. Insol in water. Miscible with most organic solvents. Polymerizes and oxidizes on standing. Concd H2SO4 forms metaindene, (C9H8)16-22.

Caution

Potential symptoms of overexposure in exptl animals are irritation of eyes, skin, mucous membranes; dermatitis, skin sensitization; liver, kidney and spleen injury; aspiration of liquid may cause chemical pneumonia. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 170.