Pigment Yellow 10

Last updated
Pigment Yellow 10
UpdatedPigmentYell10.png
Names
Other names
Benzidine Yellow 10G, Sanyo Pigment Yellow 8105
Identifiers
3D model (JSmol)
ECHA InfoCard 100.026.401 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C16H12Cl2N4O/c1-10-15(20-19-14-9-11(17)7-8-13(14)18)16(23)22(21-10)12-5-3-2-4-6-12/h2-9,15H,1H3
    Key: SYIDJAUAPDQFRN-UHFFFAOYSA-N
  • Clc1ccc(Cl)cc1N=Nc2c(C)nn(c2O)-c3ccccc3
Properties
C16H12Cl2N4O
Molar mass 347.20 g·mol−1
AppearanceYellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pigment Yellow 10 is an organic compound that is classified as a monoazopyrazolone pigment. It is used as a yellow colorant, notably as yellow road marking on highways in the US.

Pigment Yellow 10 is commonly used for yellow road markings Yellow road marking.jpg
Pigment Yellow 10 is commonly used for yellow road markings

The compound is synthesized by coupling the diazonium salt derived from dichloroaniline with the pyrazolone. [1] The structure of the dye, as determined by X-ray crystallography, consists of planar molecule with a C=O bond and two hydrazone groups. [2]

Related Research Articles

<span class="mw-page-title-main">Pigment</span> Colored material

A pigment is a powder used to add color or change visual appearance. Pigments are completely or nearly insoluble and chemically unreactive in water or another medium; in contrast, dyes are colored substances which are soluble or go into solution at some stage in their use. Dyes are often organic compounds whereas pigments are often inorganic. Pigments of prehistoric and historic value include ochre, charcoal, and lapis lazuli.

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4", as a phonetic representation of the symbols of its molecular formula.

<span class="mw-page-title-main">Azo compound</span> Organic compounds with a diazenyl group (–N=N–)

Azo compounds are organic compounds bearing the functional group diazenyl.

Iron(II) chloride, also known as ferrous chloride, is the chemical compound of formula FeCl2. It is a paramagnetic solid with a high melting point. The compound is white, but typical samples are often off-white. FeCl2 crystallizes from water as the greenish tetrahydrate, which is the form that is most commonly encountered in commerce and the laboratory. There is also a dihydrate. The compound is highly soluble in water, giving pale green solutions.

Chrome yellow is a bright, warm yellow pigment that has been used in art, fashion, and industry. It is the premier orange pigment for many applications.

<span class="mw-page-title-main">Chromophore</span> A molecule that absorbs light

A chromophore is a molecule which absorbs light at a particular wavelength and emits color as a result. Chromophores are commonly referred to as colored molecules for this reason. The word is derived from Ancient Greek χρῶμᾰ (chroma) 'color', and -φόρος (phoros) 'carrier of'. Many molecules in nature are chromophores, including chlorophyll, the molecule responsible for the green colors of leaves. The color that is seen by our eyes is that of the light not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore indicates a region in the molecule where the energy difference between two separate molecular orbitals falls within the range of the visible spectrum. Visible light that hits the chromophore can thus be absorbed by exciting an electron from its ground state into an excited state. In biological molecules that serve to capture or detect light energy, the chromophore is the moiety that causes a conformational change in the molecule when hit by light.

<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group but there are some that contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

In organic chemistry, an azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile and the activated carbon act as a nucleophile. In most cases, including the examples below, the diazonium compound is also aromatic.

Arylide yellow, also known as Hansa yellow and monoazo yellow, is a family of organic compounds used as pigments. They are primarily used as industrial colorants including plastics, building paints and inks. They are also used in artistic oil paints, acrylics and watercolors. These pigments are usually semi-transparent and range from orange-yellow to yellow-greens. Related organic pigments are the diarylide pigments. Overall, these pigments have partially displaced the toxic cadmium yellow in the marketplace. Painters such as Alexander Calder and Jackson Pollock are known to have employed arylide yellow in their artworks.

<span class="mw-page-title-main">Isoindole</span> Chemical compound

In organic chemistry and heterocyclic chemistry, isoindole consists of a benzene ring fused with pyrrole. The compound is an isomer of indole. Its reduced form is isoindoline. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in phthalocyanines, an important family of dyes. Some alkaloids containing isoindole have been isolated and characterized.

Mononitrotoluene or nitrotoluene (MNT or NT), is any of three organic compounds with the formula C6H4(CH3)(NO2). They can be viewed as nitro derivatives of toluene or as methylated derivatives of nitrobenzene.

<span class="mw-page-title-main">Diketene</span> Organic compound with formula (CH2CO)2

Diketene is an organic compound with the molecular formula C4H4O2, and which is sometimes written as (CH2CO)2. It is formed by dimerization of ketene, H2C=C=O. Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorless liquid.

<span class="mw-page-title-main">3,3'-Dichlorobenzidine</span> Chemical compound

3,3'-Dichlorobenzidine is an organic compound with the formula (C6H3Cl(NH2))2. The pure compound is pale yellow, but commercial samples are often colored. It is barely soluble in water and is often supplied as a wet paste. It is widely used in the production of diarylide yellow pigments used in the production of printing inks. Its use in the production of dyes has been largely discontinued because of concerns about carcinogenicity.

<span class="mw-page-title-main">Phthalonitrile</span> Chemical compound

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 soluble in common organic solvents. The compound is used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers.

Diarylide pigments are organic compounds that are used as pigments in inks and related materials. They often are yellow or yellow-green. To some extent, these organic compounds have displaced cadmium sulfide from the market. They exist as yellow powders of low solubility in water.

<span class="mw-page-title-main">Pigment Yellow 16</span> Chemical compound

Pigment Yellow 16 is an organic compound that is classified as a diarylide pigment.

<span class="mw-page-title-main">Acetoacetanilide</span> Chemical compound

Acetoacetanilide is an organic compound with the formula CH3C(O)CH2C(O)NHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. This chemical and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows. Acetoacetanilides usually exist as the keto-amide tautomer according to X-ray crystallography.

<span class="mw-page-title-main">Pigment Yellow 12</span> Chemical compound

Pigment Yellow 12 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 13, wherein the two phenyl groups are replaced by 2,4-xylyl.

<span class="mw-page-title-main">Pigment Yellow 13</span> Chemical compound

Pigment Yellow 13 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 12, wherein the two xylyl groups are replaced by phenyl.

<span class="mw-page-title-main">Selenosulfide</span>

In chemistry, a selenosulfide refers to distinct classes of inorganic and organic compounds containing sulfur and selenium. The organic derivatives contain Se-S bonds, whereas the inorganic derivatives are more variable.

References

  1. K. Hunger; W. Herbst (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. ISBN   978-3527306732.
  2. A. Whitaker (1988). "CI Pigment Yellow 10, 4-[2',5'-(dichlorophenyl)hydrazono]-5-methyl-2-phenyl-3H-pyrazol-3-one". Acta Crystallographica C. C44 (10): 1767–70. Bibcode:1988AcCrC..44.1767W. doi:10.1107/S0108270188006791.