Pigment Orange 13

Pigment Orange 13
Identifiers
CAS Number	3520-72-7;
3D model (JSmol)	Interactive image;
ChemSpider	30782599;
ECHA InfoCard	100.020.483
EC Number	222-530-3;
PubChem CID	135565484;
UNII	GDF7BXQ79T;
CompTox Dashboard (EPA)	DTXSID6052031 ;
	InChI InChI=1S/C32H24Cl2N8O2/c1-19-29(31(43)41(39-19)23-9-5-3-6-10-23)37-35-27-15-13-21(17-25(27)33)22-14-16-28(26(34)18-22)36-38-30-20(2)40-42(32(30)44)24-11-7-4-8-12-24/h3-18,43-44H,1-2H3 Key: LVOJOIBIVGEQBP-UHFFFAOYSA-N;
	SMILES CC1=NN(C(=C1N=NC2=C(C=C(C=C2)C3=CC(=C(C=C3)N=NC4=C(N(N=C4C)C5=CC=CC=C5)O)Cl)Cl)O)C6=CC=CC=C6;
Properties
Appearance	orange powder
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pigment Orange 13 is an organic compound and an azo compound. It is a commercial orange pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Orange 34, wherein the two phenyl groups are replaced by p-tolyl groups.^[1] Its structure has been confirmed by X-ray crystallography.^[2]

Pigment Orange 13 is a popular component of artist's paints^[3] and tattoo inks.^[4]

References

^ K. Hunger; W. Herbst (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. ISBN 978-3-527-30673-2.
^ Gorelik, Tatiana E.; Bekő, Sàndor L.; Teteruk, Jaroslav; Heyse, Winfried; Schmidt, Martin U. (2023). "Analysis of diffuse scattering in electron diffraction data for the crystal structure determination of Pigment Orange 13, C₃₂H₂₄Cl₂N₈O₂". Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials. 79 (2): 122–137. doi:10.1107/S2052520623000720. PMC 10088482. PMID 36920875.
^ Scherrer, Nadim C.; Stefan, Zumbuehl; Francoise, Delavy; Annette, Fritsch; Renate, Kuehnen (2009). "Synthetic organic pigments of the 20th and 21st century relevant to artist's paints: Raman spectra reference collection". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 73 (3): 505–524. Bibcode:2009AcSpA..73..505S. doi:10.1016/j.saa.2008.11.029. PMID 19136293.
^ Yakes, Betsy Jean; Michael, Tara Jade; Perez-Gonzalez, Marianita; Harp, Bhakti Petigara (2017). "Investigation of tattoo pigments by Raman spectroscopy". Journal of Raman Spectroscopy. 48 (5): 736–743. Bibcode:2017JRSp...48..736Y. doi:10.1002/jrs.5095.