violanthrone
{{Chembox
| ImageFile = Violanthrone.svg
| ImageSize =
| ImageAlt =
| PIN = Anthra[10,1,2-cde]benzo[rst]pentaphene-5,10-dione
| OtherNames = Dibenzanthrone, Tinon Dark Blue BOA, Ahcovat Dark Blue BO, Violanthrone A, Bianthrone A, Irgalite Blue 2R, Paradone Dark Blue
|Section1={{Chembox Identifiers
| CASNo = 116-71-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VH1DQP6QPQ
| EINECS = 204-152-0
| PubChem = 8317
| ChemSpiderID = 8015
| SMILES = c1ccc2c(c1)-c3ccc4c5ccc-6c7c5c(ccc7C(=O)c8c6cccc8)c9c4c3c(cc9)C2=O
| 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
| InChIKey = YKSGNOMLAIJTLT-UHFFFAOYAP
| StdInChI = 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
| StdInChIKey = YKSGNOMLAIJTLT-UHFFFAOYSA-N }}
|Section2={{Chembox Properties
| Formula = C34H16O2
| MolarMass = 456.48964
| Appearance = dark blue solid
| Density = 1.53 g/cm3
| MeltingPt = 492 °C (decomposes)
| BoilingPt =
| Solubility =
| MagSus = −204.8·10−6 cm3/mol
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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. {{cite journal|doi=10.1107/S0365110X64002584|title=The Crystal Structure of Violanthrone (Dibenzanthrone)|year=1964|last1=Bolton|first1=W.|last2=Stadler|first2=H. P.|journal=Acta Crystallographica|volume=17|issue=8|pages=1015–1020|bibcode=1964AcCry..17.1015B }} Isomeric with violanthrone is isoviolanthrone, which has a centrosymmetric structure.{{ Ullmann | author = Bien, H.-S. | author2 = Stawitz, J. | author3 = Wunderlich, K. | title = Anthraquinone Dyes and Intermediates | doi = 10.1002/14356007.a02_355 }}
Synthesis
It is produced by coupling of two molecules of benzanthrone.{{US patent|1993667|Manufacture of dibenzanthrone compounds}}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{{cite patent |country=CN |number=106243769 |title=A kind of preparation method of Vat Brilliant Green FFB |status=patent |inventor=Wang Hongwei, Xu Huixiang, Li Zhen, Jiang Dawei, Gao Hongyu, Guo Yuan}}{{cite journal |last1=Aoki |first1=Junji |title=Studies of Violanthrone B. I. Reduction and Oxidation of Violanthrone B |journal=Bulletin of the Chemical Society of Japan |date=December 1961 |volume=34 |issue=12 |pages=1817–1819 |doi=10.1246/bcsj.34.1817 |doi-access=free }}
