Diphenylamine

Title: Diphenylamine
CAS Registry Number: 122-39-4
CAS Name: N-Phenylbenzeneamine
Molecular Formula: C12H11N
Molecular Weight: 169.22
Percent Composition: C 85.17%, H 6.55%, N 8.28%
Line Formula: C6H5NHC6H5
Literature References: Prepd by heating aniline with aniline hydrochloride.
Properties: Crystals; floral odor. d 1.16. mp 53-54°. bp 302°. Flash pt 153°C. Discolors in light. One gram dissolves in 2.2 ml alcohol, 4.5 ml propyl alcohol; freely sol in benzene, ether, glacial acetic acid, carbon disulfide. Insol in water. Forms salts with strong acids. Keep protected from light.
Melting point: mp 53-54°
Boiling point: bp 302°
Flash point: Flash pt 153°C
Density: d 1.16
Derivative Type: Hydrochloride
Molecular Formula: C12H11N.HCl
Molecular Weight: 205.68
Percent Composition: C 70.07%, H 5.88%, N 6.81%, Cl 17.24%
Properties: Crystals, turn blue in air. Freely sol in water, alcohol.
Derivative Type: Sulfate
Molecular Formula: C12H11N.H2SO4
Molecular Weight: 267.30
Percent Composition: C 53.92%, H 4.90%, N 5.24%, S 12.00%, O 23.94%
Properties: White to yellowish powder, mp 123-125°. Practically insol in water. Sol in alc, in H2SO4.
Melting point: mp 123-125°
CAUTION: Potential symptoms of overexposure to diphenylamine are irritation of eyes, skin, mucous membranes; eczema; tachycardia, hypertension; cough, sneezing; methemoglobinemia; increased blood pressure and heart rate; proteinuria, hematuria, bladder injury. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 120.
Use: Manuf dyes; stabilizing nitrocellulose explosives and celluloid. In anal. chem for the detection of NO3, ClO3 and other oxidizing substances with which, in the presence of H2SO4, it gives a deep-blue color.
Therap-Cat-Vet: Topically in antiscrewworm mixtures. In tests for nitrate or nitrite poisoning.
Diphenylcarbazone Diphenylketene Diphenylmagnesium Diphenylpyraline Diphetarsone

Diphenylamine
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 122-39-4 YesY
ChemSpider 11003 YesY
UNII 9N3CBB0BIQ YesY
KEGG C11016 YesY
ChEBI CHEBI:4640 YesY
ChEMBL CHEMBL38688 YesY
RTECS number 9
Jmol-3D images Image 1
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
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
1
3
0
Flash point 152 °C; 306 °F; 425 K
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
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 colourless solid, but commercial samples are often yellow due to oxidized impurities.[1]Diphenylamine dissolves well in many common organic solvents, but is insoluble in water.[2] It is used mainly for its antioxidant properties.