Violanthrone

Violanthrone
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
CAS Number	116-71-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	8015;
ECHA InfoCard	100.003.775
EC Number	204-152-0;
PubChem CID	8317;
UNII	VH1DQP6QPQ ;
CompTox Dashboard (EPA)	DTXSID7026281 ;
	InChI 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;
	SMILES c1ccc2c(c1)-c3ccc4c5ccc-6c7c5c(ccc7C(=O)c8c6cccc8)c9c4c3c(cc9)C2=O;
Properties
Chemical formula	C34H16O2
Molar mass	456.48964
Appearance	dark blue solid
Density	1.53 g/cm3
Melting point	492 °C (decomposes)
Magnetic susceptibility (χ)	-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). Infobox references

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 C_2v 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]

References

^ 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.
^ 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 978-3527306732.
^ 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
^ CN patent 106243769, Wang Hongwei, Xu Huixiang, Li Zhen, Jiang Dawei, Gao Hongyu, Guo Yuan, "A kind of preparation method of Vat Brilliant Green FFB"
^ 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.

[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.

[UllmannDye-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 978-3527306732.

[3] Manufacture of dibenzanthrone compounds

[Zollinger-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] CN patent 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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