4-Aminodiphenylamine

4-Aminodiphenylamine is a diphenylamine
with an additional amine substituent. This dimer of 4-Aminodiphenylamine
aniline has various industrial uses, including as a
hair dye ingredient, but also has raised concerns
about toxicity by skin contact.[1] It is also a starting
material for the synthesis of 6PPD, an antiozonant
for various rubber products.[2] A colorimetric test
for the quantitative analysis of nitrite, at levels Names
below 100 nanograms per milliliter, is based on
nitrite-catalyzed coupling of 4- Preferred IUPAC name
aminodiphenylamine with N,N-dimethylaniline. [3] N1-Phenylbenzene-1,4-diamine

The most common route of industrial production is Other names

by the reaction of aniline with 4-Aminodiphenylamine
4‑nitrochlorobenzene followed by reduction of the p-Aminodiphenylamine
intermediate 4‑nitrodiphenylamine.[4] An N-Phenyl-p-phenylenediamine
alternative is the direct condensation reaction of
N-Phenyl-1,4-phenylenediamine
nitrobenzene with aniline via a nucleophilic
aromatic substitution of hydrogen,[5] this again PPD
requires a reduction step.[4]
Identifiers

References CAS Number 101-54-2 (https://co

mmonchemistry.cas.
1. Khanna, S. K.; Tewari, Pushpa; Joshi, Anil; org/detail?cas_rn=10
Singh, G. B. (1987). "Studies on the skin uptake
1-54-2)
and efflux kinetics of N-phenyl-p-
phenylenediamine: an aromatic amine
intermediate". International Journal of Cosmetic 3D model (JSmol) Interactive image (htt
Science. 9 (3): 137–147. doi:10.1111/j.1467- ps://chemapps.stolaf.
2494.1987.tb00470.x (https://doi.org/10.1111%2 edu/jmol/jmol.php?m
Fj.1467-2494.1987.tb00470.x). PMID 19456976 odel=C1%3DCC%3
(https://pubmed.ncbi.nlm.nih.gov/19456976). DC%28C%3DC1%2
S2CID 205555627 (https://api.semanticscholar.
9NC2%3DCC%3D
org/CorpusID:205555627).
C%28C%3DC2%29
2. Engels, Hans-Wilhelm; Weidenhaupt,
Herrmann‐Josef; Pieroth, Manfred; Hofmann, N)
Werner; Menting, Karl‐Hans; Mergenhagen,
Thomas; Schmoll, Ralf; Uhrlandt, Stefan Beilstein Reference 908935
(2007). "Rubber, 4. Chemicals and Additives".
Ullmann's Encyclopedia of Industrial Chemistry. ChEBI CHEBI:59038 (http
Weinheim: Wiley-VCH. s://www.ebi.ac.uk/ch
doi:10.1002/14356007.a23_365.pub2 (https://d
 oi.org/10.1002%2F14356007.a23_365.pub2). ebi/searchId.do?che
ISBN 978-3527306732. biId=59038)
3. Kadowaki, Ryoichi; Nakano, Shigenori;
Kawashima, Takuji (1999). "Sensitive flow ChEMBL ChEMBL572203 (htt
injection colorimetry of nitrite by catalytic ps://www.ebi.ac.uk/c
coupling of N-phenyl-p-phenylenediamine with
hembldb/index.php/c
N,N-dimethylaniline". Talanta. 48 (1): 103–107.
doi:10.1016/s0039-9140(98)00227-6 (https://do ompound/inspect/Ch
i.org/10.1016%2Fs0039-9140%2898%2900227 EMBL572203)
-6). PMID 18967448 (https://pubmed.ncbi.nlm.n
ih.gov/18967448). ChemSpider 7283 (https://www.ch
4. Bochkarev, V.V.; Soroka, L.S.; Bashkin, J.K. emspider.com/Chemi
(December 2016). "Resource-efficient cal-Structure.7283.ht
technology to produce 4-aminodiphenylamine" ml)
(https://doi.org/10.1016%2Fj.reffit.2016.10.011).
Resource-Efficient Technologies. 2 (4): 215– ECHA InfoCard 100.002.684 (https://
224. doi:10.1016/j.reffit.2016.10.011 (https://doi. echa.europa.eu/subs
org/10.1016%2Fj.reffit.2016.10.011).
tance-information/-/s
5. Stern, Michael K.; Hileman, Fredrick D.;
ubstanceinfo/100.00
Bashkin, James K. (November 1992). "The
direct coupling of aniline and nitrobenzene: a 2.684)
new example of nucleophilic aromatic
substitution for hydrogen". Journal of the EC Number 202-951-9
American Chemical Society. 114 (23): 9237–
9238. doi:10.1021/ja00049a095 (https://doi.org/ Gmelin Reference 241334
10.1021%2Fja00049a095).
PubChem CID 7564 (https://pubche
m.ncbi.nlm.nih.gov/c
ompound/7564)

RTECS number ST3150000

UNII 007X4XXS71 (http

s://precision.fda.gov/
uniisearch/srs/unii/00
7X4XXS71)

UN number 1673

CompTox Dashboard DTXSID7025895 (htt

(EPA) ps://comptox.epa.go
v/dashboard/chemic
al/details/DTXSID70
25895)

InChI [show]
InChI=1S/C12H12N2/c13-10-6-8-12(9-7-10)14
-11-4-2-1-3-5-11/h1-9,14H,13H2
Key: ATGUVEKSASEFFO-UHFFFAOYSA-N
SMILES [show]
C1=CC=C(C=C1)NC2=CC=C(C=C2)N

Properties

Chemical formula C12H12N2

Molar mass 184.242 g·mol−1

Appearance purple–black or dark

purple

Density 1.09 g/mL

Melting point 75 °C (167 °F;

348 K)

Boiling point 354 °C (669 °F;

627 K)

Hazards

GHS labelling:

Pictograms

Signal word Warning

Hazard statements H302, H317, H319,

H410

Precautionary P261, P264, P270,

statements P272, P273, P280,
P301+P312,
P302+P352,
P305+P351+P338,
P321, P330,
P333+P313,
P337+P313, P363,
P391, P501

Except where otherwise noted, data are

given for materials in their standard state (at
25 °C [77 °F], 100 kPa).
Infobox references
Retrieved from "https://en.wikipedia.org/w/index.php?title=4-Aminodiphenylamine&oldid=1195572181"