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Aniline Yellow

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Aniline Yellow
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 4-(Phenyldiazenyl)aniline
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.412 Edit this at Wikidata
EC Number
  • 200-453-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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+Key: QPQKUYVSJWQSDY-CCEZHUSRSA-N
  • 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
SMILES
  • N(=N/c1ccc(N)cc1)\c2ccccc2
Properties
Chemical formula C6H5N=NC6H4NH2 (C12H11N3)
Molar mass 197.24 g/mol
Density 1.19 g/mL
Melting point 123 to 126 °C (253 to 259 °F; 396 to 399 K)
Boiling point > 360 °C (680 °F; 633 K)
Acidity (pKa) 2.82 (25 ºC)
Magnetic susceptibility (χ) -118.3·10 cm/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Highly toxic
Suspected carcinogen
GHS labelling:
Pictograms GHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
0 2 1
Lethal dose or concentration (LD, LC):
LD50 (median dose) 200 mg/kg (mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Aniline Yellow is a yellow azo dye and an aromatic amine. It is a derivative of azobenzene. It has the appearance of an orange powder. 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, 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.

Safety

Aminoazobenzene compounds are often carcinogenic.

References

  1. "Vital staining for protozoa".
  2. Garg, Ashish; Bhat, Krishna L.; Bock, Charles W. (2002). "Mutagenicity of aminoazobenzene dyes and related structures: A QSAR/QPAR investigation". Dyes and Pigments. 55: 35–52. doi:10.1016/s0143-7208(02)00070-0.
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