Pinacyanol

Pinacyanol
Names
	IUPAC name (2E)-1-ethyl-2-[(E)-3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;chloride
	Other names Quinaldine blue
Identifiers
CAS Number	2768-90-3;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1974249;
ChemSpider	4576043;
ECHA InfoCard	100.009.182
EC Number	220-457-1;
KEGG	D05672;
PubChem CID	6364575;
UNII	91SZ6DGY86;
CompTox Dashboard (EPA)	DTXSID9046576 ;
	InChI Key: QWYZFXLSWMXLDM-UHFFFAOYSA-M; InChI=1S/C25H25N2.HI/c1-3-26-22(18-16-20-10-5-7-14-24(20)26)12-9-13-23-19-17-21-11-6-8-15-25(21)27(23)4-2;/h5-19H,3-4H2,1-2H3;1H/q+1;/p-1;
	SMILES CC[n+]1c(ccc2c1cccc2)C=CC=C3C=Cc4ccccc4N3CC.[I-];
Properties
Chemical formula	C25H25ClN2
Molar mass	388.94 g·mol−1
Appearance	blue solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pinacyanol is a cyanine dye. It is an organic cation, typically isolated as the chloride or iodide salts. The blue dye is prepared from 2-methylquinoline by quaternization with ethyl chloride or ethyl iodide. Condensation with formaldehyde results in coupling. Subsequent oxidation of the leuco intermediate gives the dye.[1] Pinacyanol is a prototypical cyanine dye that was widely used as a sensitizer in electrophotography. Its biological properties have also been investigated widely.[2]

References

Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_487.pub2.
Chong, Curtis R.; Xu, Jing; Lu, Jun; Bhat, Shridhar; Sullivan, David J.; Liu, Jun O. (2007). "Inhibition of Angiogenesis by the Antifungal Drug Itraconazole". ACS Chemical Biology. 2 (4): 263–270. doi:10.1021/cb600362d. PMID 17432820.

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[1] Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_487.pub2.

[2] Chong, Curtis R.; Xu, Jing; Lu, Jun; Bhat, Shridhar; Sullivan, David J.; Liu, Jun O. (2007). "Inhibition of Angiogenesis by the Antifungal Drug Itraconazole". ACS Chemical Biology. 2 (4): 263–270. doi:10.1021/cb600362d. PMID 17432820.