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o-Aminoazotoluene

analytical standard

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Synonym(s):
4′-Amino-2,3′-dimethylazobenzene, Solvent Yellow 3
Linear Formula:
CH3C6H4N=NC6H3(CH3)NH2
CAS Number:
97-56-3
Molecular Weight:
225.29
Beilstein:
6506005
EC Number:
202-591-2
MDL number:
MFCD00007733
UNSPSC Code:
41116107
PubChem Substance ID:
329753852
NACRES:
NA.24

grade

analytical standard

Quality Level

100

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

101-102 °C (lit.)

application(s)

cleaning products
cosmetics
environmental
food and beverages
personal care

format

neat

SMILES string

Cc1ccccc1\N=N\c2ccc(N)c(C)c2

InChI

1S/C14H15N3/c1-10-5-3-4-6-14(10)17-16-12-7-8-13(15)11(2)9-12/h3-9H,15H2,1-2H3/b17-16+

InChI key

PFRYFZZSECNQOL-WUKNDPDISA-N

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General description

o-Aminoazotoluene (AAT) is categorized as a Class 2B carcinogen by the international agency for research on cancer (IARC). This class of azo dyes are widely used as colorants in a variety of products including leather, cosmetics, paper, toys, plastics, pharmaceuticals, textiles, paints, food, leather, etc. Primary aromatic amines (PAAs) are most commonly used as starting compounds in the production of azo dyes and can often migrate into foodstuffs from food packaging materials. AAT finds applications in coloring oils, fats, and waxes.
o-Aminoazotoluene (AAT) is a carcinogenic primary amino azo dye.1

Application

o-Aminoazotoluene may be used as an analytical reference standard for the quantification of the analyte in:
  • Dyes, cosmetics, inks and finger paints using liquid chromatography coupled to mass spectrometry (LC-MS).
  • Commercial samples including food packaging plastic, multilayer plastic laminates and recycled paperboard categories using liquid chromatography coupled to mass spectrometry (LC-MS) technique.

AAT has been used as reference standard in determination of aromatic amines from azo colorants in toys using HPLC.2
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Caution

Restricted to professional users. Attention − Avoid exposure − obtain special instructions before use.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H315,H317,H319,H350

Hazard Classifications

Acute Tox. 3 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Genotoxicity of o-aminoazotoluene (AAT) determined by the Ames test, the in vitro chromosomal aberration test, and the transgenic mouse gene mutation assay
Ohsawa I-K, et al.
Mutation Research. Genetic Toxicology and Environmental Mutagenesis, 471(1-2), 113-126 (2000)
Yoko Uematsu et al.
Journal of AOAC International, 100(4), 1102-1109 (2017-02-27)
A method for simutaneously detecting 8 oil-soluble and 10 water-soluble (3 basic and 7 acidic) illegal dyes in foods was developed. The sample was mixed with water, followed by methanol and tetrahydrofuran. Transesterification with sodium methoxide was applied to the
Reliable liquid chromatography?mass spectrometry method for investigation of primary aromatic amines migration from food packaging and during industrial curing of multilayer plastic laminates
Lambertini F, et al.
Journal of Mass Spectrometry : Jms, 49(9), 870-877 (2014)
B G Lake et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 39(10), 999-1011 (2001-08-29)
The ability of furfural to induce unscheduled DNA synthesis (UDS) in hepatocytes of male and female B6C3F(1) mice and male F344 rats after in vivo administration and in vitro in precision-cut human liver slices has been studied. Preliminary toxicity studies
M Y Pakharukova et al.
Bulletin of experimental biology and medicine, 144(3), 338-341 (2008-05-07)
Selective increase of DNA-binding activity of constitutive androstane receptor was detected in rat and mouse liver in response to aminoazo dyes exhibiting hepatocarcinogenic activity for these species (ortho-aminoazotoluene for mice and 3'-methyl-4-dimethylaminobenzene for rats). Competition of azo dyes with 3H-5alpha-androst-16-ene-3alpha-ol
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