Violanthrone

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Violanthrone
Violanthrone.svg
Names
Preferred IUPAC name
Anthra[10,1,2-cde]benzo[rst]pentaphene-5,10-dione
Other names
Dibenzanthrone, Tinon Dark Blue BOA, Ahcovat Dark Blue BO, Violanthrone A, Bianthrone A, Irgalite Blue 2R, Paradone Dark Blue
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.775 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-152-0
PubChem CID
UNII
  • InChI=1S/C34H16O2/c35-33-25-7-3-1-5-17(25)19-9-11-21-22-12-10-20-18-6-2-4-8-26(18)34(36)28-16-14-24(30(22)32(20)28)23-13-15-27(33)31(19)29(21)23/h1-16H
    Key: YKSGNOMLAIJTLT-UHFFFAOYSA-N
  • InChI=1/C34H16O2/c35-33-25-7-3-1-5-17(25)19-9-11-21-22-12-10-20-18-6-2-4-8-26(18)34(36)28-16-14-24(30(22)32(20)28)23-13-15-27(33)31(19)29(21)23/h1-16H
    Key: YKSGNOMLAIJTLT-UHFFFAOYAP
  • c1ccc2c(c1)-c3ccc4c5ccc-6c7c5c(ccc7C(=O)c8c6cccc8)c9c4c3c(cc9)C2=O
Properties
C34H16O2
Molar mass 456.48964
Appearancedark blue solid
Density 1.53 g/cm3
Melting point 492 °C (decomposes)
−204.8·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Violanthrone, also known as dibenzanthrone, is an organic compound that serves as a vat dye and a precursor to other vat dyes. X-ray crystallography confirms that the molecule is planar with C2v symmetry. [1] Isomeric with violanthrone is isoviolanthrone, which has a centrosymmetric structure. [2]

Synthesis

It is produced by coupling of two molecules of benzanthrone. [3] [4] [5] [6]

Synthesis Violanthrone V2.svg

References

  1. ↑ Bolton, W.; Stadler, H. P. (1964). "The Crystal Structure of Violanthrone (Dibenzanthrone)". Acta Crystallographica. 17 (8): 1015–1020. Bibcode:1964AcCry..17.1015B. doi:10.1107/S0365110X64002584.
  2. ↑ Bien, H.-S.; Stawitz, J.; Wunderlich, K. "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. ISBN   978-3-527-30673-2.
  3. ↑ Manufacture of dibenzanthrone compounds
  4. ↑ Heinrich Zollinger, Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments, 3rd edition, Wiley-VCH, Weinheim, 2003, ISBN   3-906390-23-3, p. 291
  5. ↑ CNpatent 106243769,Wang Hongwei, Xu Huixiang, Li Zhen, Jiang Dawei, Gao Hongyu, Guo Yuan,"A kind of preparation method of Vat Brilliant Green FFB"
  6. ↑ Aoki, Junji (December 1961). "Studies of Violanthrone B. I. Reduction and Oxidation of Violanthrone B". Bulletin of the Chemical Society of Japan. 34 (12): 1817–1819. doi: 10.1246/bcsj.34.1817 .
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