Diphenylamine

Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

Diphenylamine
Names
Preferred IUPAC name
N-Phenylaniline
Other names
(Diphenyl)amine
Diphenylamine (deprecated)
Diphenylazane
N-Phenylbenzenamine
Anilinobenzene
(Phenylamino)benzene
N,N-Diphenylamine
C.I. 10355
Phenylbenzenamine
Identifiers
3D model (JSmol)
Abbreviations DPA
508755
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.128
EC Number
  • 204-539-4
67833
KEGG
PubChem CID
RTECS number
  • JJ7800000
UNII
UN number 2811 3077
  • InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H Y
    Key: DMBHHRLKUKUOEG-UHFFFAOYSA-N Y
  • InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
    Key: DMBHHRLKUKUOEG-UHFFFAOYAJ
SMILES
  • c1ccc(cc1)Nc2ccccc2
Properties
C12H11N
Molar mass 169.23 g/mol
Appearance White, off-white
Odor Floral
Density 1.2 g/cm3
Melting point 53 °C (127 °F; 326 K)
Boiling point 302 °C (576 °F; 575 K)
0.03%
Vapor pressure 1 mmHg (108°C)
Acidity (pKa) 0.79
Magnetic susceptibility (χ)
 -109.7·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic. Possible mutagen. Possible teratogen. Harmful in contact with skin, and if swallowed or inhaled. Irritant.
GHS labelling:
Danger
H301, H311, H319, H331, H373, H410
P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P314, P321, P322, P330, P337+P313, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
3
1
0
Flash point 152 °C (306 °F; 425 K)
NIOSH (US health exposure limits):
PEL (Permissible)
 none
REL (Recommended)
 TWA 10 mg/m3
IDLH (Immediate danger)
 N.D.
Related compounds
Related Amine
 Aniline
Supplementary data page
Diphenylamine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
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