Diphenylamine

Diphenylamine
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
N-Phenylaniline[1]
Other names
(Diphenyl)amine
Diphenylamine (deprecated[1])
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 Edit this at Wikidata
EC Number
  • 204-539-4
67833
KEGG
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 checkY
    Key: DMBHHRLKUKUOEG-UHFFFAOYSA-N checkY
  • InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
    Key: DMBHHRLKUKUOEG-UHFFFAOYAJ
  • c1ccc(cc1)Nc2ccccc2
Properties
C12H11N
Molar mass 169.23 g/mol
Appearance White, off-white[2]
Odor Floral[3]
Density 1.2 g/cm3
Melting point 53 °C (127 °F; 326 K)
Boiling point 302 °C (576 °F; 575 K)
0.03%[3]
Vapor pressure 1 mmHg (108°C)[3]
Acidity (pKa) 0.79[4]
-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:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 152 °C (306 °F; 425 K)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 TWA 10 mg/m3[3]
IDLH (Immediate danger)
 N.D.[3]
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).
checkY verify (what is checkY☒N ?)

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.[5] Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water.[6] 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.[7]

  1. ^ a b International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 671. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ https://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/24/242586/242586-BULK_______SIAL_____.pdf [bare URL PDF]
  3. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0240". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "Diphenylamine".
  5. ^ P. F. Vogt, J. J. Gerulis, "Amines, Aromatic" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_037
  6. ^ "Conclusion on the peer review of the pesticide risk assessment of the active substance diphenylamine". EFSA Journal. 10: 2486. 25 January 2012. doi:10.2903/j.efsa.2012.2486.
  7. ^ Safe, S.; Hutzinger, O.; Crocker, J. F. S.; Digout, S. C. (1977). "Identification of toxic impurities in commercial Diphenylamine". Bulletin of Environmental Contamination and Toxicology. 17 (2): 204–207. Bibcode:1977BuECT..17..204S. doi:10.1007/BF01685551. PMID 843636.