Aniline Yellow

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

* 60-09-3 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:233869 Y

ChEMBL |

* ChEMBL83761 Y

ChemSpider |

* 5828 Y

EC Number |

* 200-453-6

KEGG |

* C19187 Y

PubChem CID

* 6051

UNII |

* 57X2AH42T1 Y

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

SMILES

* N(=N/c1ccc(N)cc1)\c2ccccc2

Properties

Chemical formula

| C6H5N=NC6H4NH2
Molar mass | 197.24 g/mol
Melting point |  123 to 126 °C (253 to 259 °F; 396 to 399 K)
Boiling point | > 360 °C (680 °F; 633 K)

Magnetic susceptibility (χ)

| -118.3·10−6 cm3/mol
Hazards
Main hazards | Highly toxic
Cancer suspect agent
NFPA 704 (fire diamond)  |

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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,[1] 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.[2]

## References

1. ↑ "Vital staining for protozoa". http://www.microscopy-uk.org.uk/mag/artfeb00/rhvital.html.
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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*[CID]: Compound ID