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Properties of substance:

1,3-indandione

Group of substances:

organic

Physical appearance:

needles crystals

Empirical formula (Hill's system for organic substances):

C9H6O2

Melting point (°C):

130-131

CAS ¹: 606-23-5

Solubility (g/100 g of solvent):

benzene: soluble (hot) [Ref.]
ethanol: soluble (hot) [Ref.]
water: sparingly soluble [Ref.]

Synthesis 1:

Reference: Teeters, W. O., & Shriner, R. L. A New Preparation of Ninhydrin / Journal of the American Chemical Society. - 1933. - Vol. 55, No. 7 pp. 3027 [doi: 10.1021/ja01334a072]

To a 3-liter beaker containing 1200—1500 cc. of hot water was added 100 g. of 2-(ethoxycarbonyl)-1,3-indandione sodium salt. The solution was cooled to 70° and with vigorous agitation the sodium salt was decomposed with 100 cc. of sulfuric acid solution (3 parts of concentrated sulfuric acid and 1 part of water). The mixture was cooled in an icebath to 15° and filtered. The product when dry weighed 59 g. (99% of the theoretical). The total 1,3-indandione obtained from 500 g. of diethyl phthalate was 236 g. of a pale yellow solid; m. p. 127—129°. Recrystallization from dioxane-benzene mixture by addition of petroleum ether yielded long glistening needles, m. p. 130—131°, which checked the value given by Wislicenus.

References:

  1. Dictionary of organic compounds. - vol.1, Abietic acid - Dypnone. - London, 1946. - pp. 877

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru