Aromatic amines

Aromatic amines are amines with an aromatic substituent ; H. the NH ₂ , NH or N groups are bonded to an aromatic hydrocarbon atom. The simplest example of an aromatic amine is aniline .

properties

Protonated aromatic amines, usually have a lower pK _s value - are so sour - non-aromatic than their analogues. This effect is based on the delocalization of the free electrons of nitrogen over the aromatic ring.

Representative aniline relatives
Aromatic amine		CAS number	properties	use
aniline		62-53-3
o -Toluidine		95-53-4
2,4,6-trimethylaniline		88-05-1
o -anisidine		90-04-0
3-trifluoromethylaniline		98-16-8		Intermediate product for herbicides , metabolite
N -methylaniline		100-61-8

Humans are aromatic amines v. a. through their diet (e.g. through pesticides ), pharmaceuticals (e.g. prilocaine ), hair dyes , cigarette smoke and diesel fumes. In professional life there is a higher burden u. a. in the rubber, textile and paint industries.

Naming

Numerous aromatic amines derive their name from a parent compound by adding the ending -idin . The result of anisole  (methoxybenzene) by adding the amino substituents, and this extension is the name Anis idin from phenetole  (ethoxybenzene) the Phenet idin from toluene the Tolu idin from xylene the Xyl idin from mesitylene the Mes idin from pseudocumene the Pseudocum idin etc.

Primary aromatic amines

Primary aromatic amines (PAA) are known to some extent as human carcinogens . This includes B. 2-naphthylamine . Other PAA are considered carcinogenic based on animal studies. These include B. o -anisidine and o -toluidine .

Individual evidence

1. ↑ A. Seidel: Exposure to Aromatic Amines - Overview on Chemistry ( Memento of February 16, 2015 in the Internet Archive ), presentation of November 9, 2009, accessed on September 24, 2012.
2. ↑ BfR: Primary aromatic amines from printed food contact articles such as serviettes or baker's bags , Opinion No. 021/2014 of July 24, 2013.