Aniline Yellow

Aniline Yellow
IUPAC name 4-Phenyldiazenylaniline
Other names para-aminoazobenzene 4-phenylazoaniline AAB Brasilazina oil Yellow G Ceres Yellow Fast spirit Yellow Induline R Oil Yellow AAB Oil Yellow AN Oil Yellow B Oil Yellow 2G Oil Yellow R Organol Yellow Organol Yellow 2A Solvent Yellow Somalia Yellow 2G Stearix Brown 4R Sudan Yellow R Sudan Yellow RA C.I. 11000
Identifiers
CAS number	60-09-3 Y
PubChem	6051
ChemSpider	5828 Y
EC number	200-453-6
KEGG	C19187 Y
ChEBI	CHEBI:233869 Y
ChEMBL	CHEMBL83761 Y
Jmol-3D images	Image 1
SMILES N(=N/c1ccc(N)cc1)\c2ccccc2
InChI InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+ Y Key: QPQKUYVSJWQSDY-CCEZHUSRSA-N Y InChI=1/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+ Key: QPQKUYVSJWQSDY-CCEZHUSRBB
Properties
Molecular formula	C6H5N=NC6H4NH2
Molar mass	197.24 g/mol
Melting point	123-126 °C
Boiling point	> 360 °C
Hazards
Main hazards	Highly toxic Cancer suspect agent
NFPA 704	2 0 1
Y Yellow (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aniline Yellow is a yellow azo dye and an aromatic amine. It is a derivate of azobenzene. It has the appearance of an orange powder. It is a carcinogen.^[1]

Aniline Yellow was the first azo dye. it was first produced in 1861 by C. Mene. The second azo dye was Bismarck Brown in 1863. Aniline Yellow was commercialized in 1864 as the first commercial azo dye, a year after Aniline Black. It is manufactured from aniline.

Uses

Aniline Yellow is used in microscopy for vital staining,^[2] in pyrotechnics for yellow colored smokes, in yellow pigments and inks including inks for inkjet printers. It is also used in insecticides, lacquers, varnishes, waxes, oil stains, and styrene resins. It is also an intermediate in synthesis of other dyes, e.g. chrysoidine, indulines, Solid Yellow, and Acid Yellow.

Toxic oil syndrome

Aniline Yellow was involved in the 1981 Spanish Toxic Oil Syndrome (TOS). A Madrid-based company imported denaturated rapeseed oil, dyed by aniline yellow to mark it as unsuitable for human consumption, to be used as a fuel in steel mills. However, the company distilled the oil to remove the dye, and sold it as a much more valuable olive oil for cooking. The result was a rash of pneumonia-type illnesses, with a second stage with lesions, weight loss, paralysis, and muscle wasting. The net result was over 20,000 sick and 400 dead. The chemistry of the poisonous reaction is still subject of a debate.^[3]

References

1. ^ http://msds.chem.ox.ac.uk/PH/4-phenylazoaniline.html
2. ^ http://www.microscopy-uk.org.uk/mag/artfeb00/rhvital.html
3. ^ http://www.researchinformation.co.uk/fse/fse0301/0301issue.php