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Diphenylamine

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Revision as of 13:44, 17 February 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (no changed fields - added verified revid - updated 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProj)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Diphenylamine
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name Diphenylamine
Other names N-Phenylbenzenamine;
N-Phenyl Aniline;
DPA;
Anilinobenzene;
(phenylamino)benzene;
N,N-diphenylamine;
big dipper;
C.I. 10355;
Phenylbenzenamine;
Diphenylamine;
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.128 Edit this at Wikidata
KEGG
RTECS number
  • 9
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13HKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N
  • InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13HKey: DMBHHRLKUKUOEG-UHFFFAOYAJ
SMILES
  • c1ccc(cc1)Nc2ccccc2
Properties
Chemical 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
Occupational safety and health (OHS/OSH):
Main hazards Toxic. Possible mutagen. Possible teratogen. Harmful in contact with skin, and if swallowed or inhaled. Irritant.
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
Related compounds
Supplementary data page
Diphenylamine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Diphenylamine is the organic compound with the formula (C6H5)2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities.

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. With strong acids, it forms the water soluble salt.

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.

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.

(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.

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

References

  1. P. F. Vogt, J. J. Gerulis, “Amines, Aromatic” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.
  2. "Apple Scald, a Complex Problem" W.J. Bramlage (University of Massachusetts Department of Plant and Soil Sciences) Post Harvest Pomology Newsletter, 6(2): 11-14 September 1988 http://postharvest.tfrec.wsu.edu/pgDisplay.php?article=N6I2C
  3. T. Kahl, K.-W. Schröder, F. R. Lawrence, W. J. Marshall, Hartmut Höke, Rudolf Jäckh, "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.
  4. F. D. Hager (1941). "Triphenylamine". Organic Syntheses; Collected Volumes, vol. 1, p. 544.

External links

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