Diphenylamine is manufactured by the thermal deamination of aniline over oxide

catalysts:

2 C6H5NH2 → (C6H5)2NH + NH3

It is a weak base, with a Kb of 10−14. With strong acids, it forms the water soluble salt.

[edit] Applications
Diphenylamine is used as a pre- or postharvest scald inhibitor for apples. Its anti-scald
activity is the result of its antioxidant properties, which protect the apple skin from the
oxidation products of alpha-farnesene during storage.[2]

Diphenylamine derivatives are also useful. Ring-alkylated derivatives of diphenylamine

are used as "antiozinates" in the manufacture of rubber products, reflecting the
antioxidant nature of aniline derivatives. The compound undergoes various cyclisaton
reactions. With sulfur, it gives phenothiazine, a precursor to certain pharmaceuticals.[3]

(C6H5)2NH + 2 S → S(C6H4)2NH + H2S

With iodine, it cyclises to carbazole:

(C6H5)2NH + I2 → (C6H4)2NH + 2 HI
Arylation with iodobenzene gives triphenylamine.[4]

Diphenylamine finds niche use as a test for nitrates (see nitrate test).

[edit] ReferencesDiphenylamine

IUPAC name[hide]Diphenylamine
Other names[hide]N-Phenylbenzenamine;
N-Phenyl Aniline;
DPA;
Anilinobenzene;
(phenylamino)benzene;
N,N-diphenylamine;
big dipper;
C.I. 10355;
Phenylbenzenamine;
Diphenylamine;
Identifiers
CAS number 122-39-4 Y
ChemSpider 11003
UNII 9N3CBB0BIQ Y
RTECS number 9
SMILES [show]c1ccc(cc1)Nc2ccccc2
InChI [show]InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChI key [show]DMBHHRLKUKUOEG-UHFFFAOYAJ
Properties
Molecular formula C12H11N
Molar mass 169.23 g/mol
Appearance White crystals
Density 1.2 g/cm³
Melting point 53 °C (326 K)

Boiling point 302 °C (575 K)

Solubility in water Slightly

Hazards
MSDS External MSDS
R-phrases R23 R24 R25 R33 R50 R53
S-phrases S36 S37 S45 S60 S61
NFPA 704 130
Flash point 152°C
Related compounds
Related Amine Aniline
Supplementary data page
Structure and
properties n, εr, etc.
Thermodynamic
data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Y (what is this?) (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25
°C, 100 kPa)
Infobox references

Diphenylamine is the organic compound with the formula (C6H5)2NH. It is a colourless

solid, but samples are often yellow due to oxidized impurities.[1]

Contents [hide]
1 Preparation and reactivity
2 Applications
3 References
4 External links

[edit] Preparation and reactivity

Diphenylamine is manufactured by the thermal deamination of aniline over oxide
catalysts:

2 C6H5NH2 → (C6H5)2NH + NH3

It is a weak base, with a Kb of 10−14. With strong acids, it forms the water soluble salt.
[edit] Applications
Diphenylamine is used as a pre- or postharvest scald inhibitor for apples. Its anti-scald
activity is the result of its antioxidant properties, which protect the apple skin from the
oxidation products of alpha-farnesene during storage.[2]