Pigment yellow 139 is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
that is used as a yellow-orange pigment. It is classified as a derivative of
isoindoline
Isoindoline is a heterocyclic organic compound with the molecular formula C8H9N. The parent compound has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound's structure is ...
. This yellow-orange solid is virtually insoluble in most solvents.
[K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. ]
The species is prepared by addition of ammonia to o-
phthalonitrile
Phthalonitrile is an organic compound with the formula C6H4(CN)2, which is an off-white crystal solid at room temperature. It is a derivative of benzene, containing two adjacent nitrile groups. The compound has low solubility in water but is sol ...
to give the
diiminoisoindoline, which in turn condenses with
barbituric acid
Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid ...
.
[Volker Radtke, Peter Erk andBenno Sens "Isoindoline Pigments" in Edwin B. Faulkner, Russell J. Schwartz in High Performance Pigments. Edited by Edwin B. Faulkner and Russell J. Schwartz, Wiley-VCH, Weinheim. 2009. ]
References
External links
{{Commons category, Pigments
Pigment Yellow 139
Pigments
Organic pigments
Shades of yellow