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. ISBN 978-3527306732.
^ 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.

[1] Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_487.pub2. ISBN 978-3527306732.

[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.

[1]

[2]