CAS number 122-39-4 YesY
ChemSpider 11003 YesY
KEGG C11016 YesY
RTECS number 9
Jmol-3D images Image 1
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
MSDS External MSDS
R-phrases R23 R24 R25 R33 R50 R53
S-phrases S36 S37 S45 S60 S61
Main hazards Toxic. Possible mutagen. Possible teratogen. Harmful in contact with skin, and if swallowed or inhaled. Irritant.
NFPA 704
NFPA 704.svg
Flash point 152°C
Related compounds
Related Amine Aniline
Supplementary data page
Structure and
n, εr, etc.
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
 YesY (verify) (what is: YesY/N?)
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]


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.


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).


  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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0544 ; Coll. Vol. 1: 544 

External links

Wikimedia Foundation. 2010.

Поможем решить контрольную работу

Look at other dictionaries:

  • Diphénylamine — Général Synonymes C.I. 10355 N Phénylaniline Anilinobenzène No CAS …   Wikipédia en Français

  • diphenylamine — diphenylamine; hexa·ni·tro·diphenylamine; thio·diphenylamine; …   English syllables

  • diphénylamine — ● diphénylamine nom féminin Arylamine secondaire (C6H5)2NH. (Solide fondant à 53 °C, c est un intermédiaire pour la synthèse de colorants et un stabilisant de la nitrocellulose.) …   Encyclopédie Universelle

  • diphenylamine — [dī fen΄əl ə mēn′, dīfēn΄əl ə mēn′; dī fen΄əl am′ēn, dī fēn΄əam′ēn΄, dī fēn΄ə am′in] n. [ DIPHENYL + AMINE] a colorless, crystalline chemical compound, (C6H5) 2NH, used as a stabilizer of explosives and propellants, as a test for nitric acid, and …   English World dictionary

  • diphenylamine —    Chemical reagent used in solution with sulfuric acid and acetic acid in the dermal nitrate test. Diphenylamine is also used in smokeless powder as a stabilizer to inhibit decomposition …   Forensic science glossary

  • Diphenylamine (data page) — This article is about Diphenylamine Material Safety Data Sheet (MSDS). For the main article see Diphenylamine. Contents 1 Physical data 2 Toxicology 3 Risk phrases 4 Transport infor …   Wikipedia

  • diphenylamine — noun Etymology: International Scientific Vocabulary Date: 1872 a crystalline pleasant smelling compound (C6H5)2NH used chiefly in the manufacture of dyes and as an indicator …   New Collegiate Dictionary

  • diphenylamine — /duy fen l euh meen , am in, feen /, n. Chem. a colorless, crystalline, slightly water soluble benzene derivative, C12H11N, used chiefly in the preparation of various dyes, as a stabilizer for nitrocellulose propellants, and for the detection of… …   Universalium

  • diphenylamine — noun an aromatic amine, (CH)NH, used in the manufacture of plastics, dyes, explosives, pesticides, fungicides and pharmaceuticals …   Wiktionary

  • diphenylamine — di·phe·nyl·amine (.)dī .fen əl ə mēn, .fēn , əl am ən n a crystalline pleasant smelling compound (C6H5)2NH that has been used in veterinary medicine, in the manufacture of dyes, and in stabilizing explosives * * * di·phen·yl·amine (di… …   Medical dictionary

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”