1-naphthylamine

from Wikipedia, the free encyclopedia
Structural formula
Structural formula 1-naphthylamine
General
Surname 1-naphthylamine
other names
  • 1-aminonaphthalene
  • α-naphthylamine
Molecular formula C 10 H 9 N
Brief description

light brown solid with an amine-like odor

External identifiers / databases
CAS number 134-32-7
EC number 205-138-7
ECHA InfoCard 100.004.672
PubChem 8640
Wikidata Q161655
properties
Molar mass 143.19 g mol −1
Physical state

firmly

density

1.17 g cm −3

Melting point

50 ° C

boiling point

300 ° C

solubility
  • heavy in water (2 g l −1 at 20 ° C)
  • good in alcohol and ether
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-411
P: 264-273-281-301 + 312
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-naphthylamine is a derivative of naphthalene . It belongs to the group of aromatic amino compounds . In addition to 1-naphthylamine, there is also the isomer 2-naphthylamine , which harbors considerable health risks.

Extraction and presentation

Historical

Nikolay Zinin received 1-naphthylamine (he Naphtalidam called) from 1-nitronaphthalene by reduction with ammonium sulfide .

Technically

It is obtained on an industrial scale by nitrating naphthalene with nitrating acid ( nitric acid with sulfuric acid ) to give 1-nitronaphthalene in a discontinuous stirred tank. After separation, the nitronaphthalene is reduced to 1-naphthylamine with iron .

use

1-Naphthylamine is used for the synthesis of azo dyes and herbicides, aminonaphthalene sulfonic acids, -naphthol and N- phenyl-1-naphthylamine (an antioxidant for rubber). It is also used to detect nitrite with Lunge's reagent .

Reaction scheme for the reaction of the lung reagent with nitrite. By adding 2-3 drops of lung I and II, the sulfanilic acid  ( 1 ) first forms a diazonium salt  ( 2 ), which further reacts with 1-naphthylamine ( 3 ) to form an azo dye  ( 4 ) and quickly turns the solution red .

Individual evidence

  1. ↑ a b c d e f g Entry on 1-naphthylamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ a b Toxicological assessment of α-naphthylamine (PDF) at the professional association for raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
  3. ↑ Entry on 1-naphthylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ N. Zinin: Description of some organic bases. In: Journal for practical chemistry . 1842, 27, pp. 140–153 ( limited preview in Google book search).

literature