1,7-dihydroxyanthraquinone

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Structural formula
Structure of 1,7-dihydroxyanthraquinone
General
Surname 1,7-dihydroxyanthraquinone
other names
  • 1,7-dihydroxy-9,10-anthracenedione
  • 1,7-dihydroxy-9,10-anthraquinone
Molecular formula C 14 H 8 O 4
External identifiers / databases
CAS number 569-08-4
PubChem 14886011
Wikidata Q43686410
properties
Molar mass 240.21 g mol −1
Melting point

292 ° C

solubility
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,7-Dihydroxyanthraquinone , also known under the name m -dihydroxyanthraquinone, is an organic compound from the group of anthraquinones , more precisely the dihydroxyanthraquinones .

presentation

The 1,7-dihydroxyanthraquinone can be prepared from the product ( 3 ) of a Diels-Alder reaction , a diene ( 1 ) and a derivative of juglone ( 2 ) in benzene . Adding concentrated hydrochloric acid in chloroform followed by ethanol gives a yield of approximately 75-80%.

OAc = acetoxy group

1,7-Dihydroxyanthraquinone can also be produced by reacting a benzophenone derivative in a molten salt .

1,7-Dihydroxyanthraquinone ÜV2.2.svg

Individual evidence

  1. ↑ a b Brian Beagley, Anthony DM Curtis, Robin G. Pritchard, Richard J. Stoodley: Highly regio- and stereo-selective Diels-Alder reactions of 5- (2 ', 3', 4 ', 6'-tetra-O -acetyl-β-D-glucopyranosyloxy) -1,4-naphthoquinone. In: J. Chem. Soc., Chem. Commun. 1991, pp. 119-121, doi : 10.1039 / C39910000119 .
  2. ↑ a b 2nd chlorine dim . In: Ian Heilbron (Ed.): Dictionary of organic Compounds . tape 2 . Eyre & Spottiswoode, Ltd, London 1965, ISBN 0-413-60700-3 , pp. 1050 .
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ^ Andre Wahl, FW Atack: The Manufacture Of Organic Dyestuffs . G. Bell and Sons, Limited. 1919. Retrieved June 26, 2017.
  5. ↑ Vanessa Gonnot, Cyril Antheaume, Marc Nicolas, Charles Mioskowski, Rachid Baati: Highly Selective Three-Step Synthesis of Rhein in Chloroaluminate Molten Salt: Preclusion of the Hayashi Rearrangement. In: European Journal of Organic Chemistry . , 2009, pp. 6205-6210, doi : 10.1002 / ejoc.200900960 .