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| Diphenylamine | |
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| 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 | [122-39-4] |
| RTECS number | 9 |
| SMILES |
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| 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 |
| Main hazards | Toxic. Possible mutagen. Possible teratogen. Harmful in contact with skin, and if swallowed or inhaled. Irritant. |
| NFPA 704 |
 1
3
0
|
| R-phrases | R23 R24 R25 R33 R50 R53 |
| S-phrases | S36 S37 S45 S60 S61 |
| 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 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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 |
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.
Applications
Diphenylaniline itself has few applications but its derivatives are more 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.[2]
- (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.[3]
Safety
Diphenylamine, like other arylamines, is toxic. Exposure is highly regulated in most countries. See MSDS.
References
- ^ P. F. Vogt, J. J. Gerulis, “Amines, Aromatic” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.
- ^ 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.
- ^ F. D. Hager (1941). "Triphenylamine". Org. Synth.; Coll. Vol. 1: 544.
External links
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- This page was last modified on 30 July 2008, at 17:26.
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