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Merck
CN

31629

o-Aminoazotoluene

analytical standard

Synonym(s):

4′-Amino-2,3′-dimethylazobenzene, Solvent Yellow 3

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About This Item

Linear Formula:
CH3C6H4N=NC6H3(CH3)NH2
CAS Number:
97-56-3
Molecular Weight:
225.29
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329753852
EC Number:
202-591-2
Beilstein/REAXYS Number:
6506005
MDL number:
MFCD00007733

Key Documents

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Product Name

o-Aminoazotoluene, analytical standard

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

SMILES string

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

grade

analytical standard

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

Quality Level

100

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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.

Disclaimer

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

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.
This compound is listed in the SVHC (Substances of very high concern) candidate list of ECHA (European Chemicals Agency)
o-Aminoazotoluene (AAT) is a carcinogenic primary amino azo dye.1

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8887
BCCF0279
BCBR8036V

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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)
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)
S I Il'nitskaya et al.
Bulletin of experimental biology and medicine, 137(6), 548-550 (2004-09-30)
Suckling mice were more sensitive to the hepatocarcinogenic effect of various carcinogens compared to adult animals. After treatment with o-aminoazotoluene and diethylnitrosamine HNF3-DNA-binding capacity and glucocorticoid-induced liver tyrosine aminotransferase activity in suckling mice decreased more significantly than in adult animals.
Anuradha Mishra et al.
Journal of hazardous materials, 118(1-3), 213-217 (2005-02-22)
In this study, the application of a food grade polysaccharide namely Plantago psyllium mucilage has been assessed for the removal of dyes from model textile wastewater containing golden yellow (C.I. Vat Yellow 4) and reactive black (C.I. Reactive Black 5).
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