Triphenylamine

Triphenylamine
Names
Preferred IUPAC name
N,N-Diphenylaniline
Other names
Triphenylamine
N,N,N-Triphenylamine
N,N-Diphenylbenzeneamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.123 Edit this at Wikidata
EC Number
  • 210-035-5
RTECS number
  • YK2680000
UNII
  • InChI=1S/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H checkY
    Key: ODHXBMXNKOYIBV-UHFFFAOYSA-N checkY
  • InChI=1/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
    Key: ODHXBMXNKOYIBV-UHFFFAOYAF
  • c3c(N(c1ccccc1)c2ccccc2)cccc3
Properties
C18H15N
Molar mass 245.325 g·mol−1
Appearance Off-white solid
Density 0.774 g/cm3
Melting point 127 °C (261 °F; 400 K)
Boiling point 347 to 348 °C (657 to 658 °F; 620 to 621 K)
Almost insoluble
log P 5.74
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Flash point 180 °C (356 °F; 453 K) open cup
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 5 mg/m3[1]
IDLH (Immediate danger)
 N.D.[1]
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 ?)

Triphenylamine is an organic compound with formula (C6H5)3N. In contrast to most amines, triphenylamine is nonbasic. At room temperature it appears as a colorless crystalline solid, with monoclinic structure. It is well miscible in diethyl ether and benzene, but it is practically insoluble in water, and partially in ethanol. Its derivatives have useful properties in electrical conductivity and electroluminescence, and they are used in OLEDs as hole-transporters.[2]

Triphenylamine can be prepared by arylation of diphenylamine.[3]

  1. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0643". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Wei Shi, Suqin Fan, Fei Huang, Wei Yang, Ransheng Liu and Yong Cao "Synthesis of Novel Triphenylamine-based Conjugated Polyelectrolytes and Their Application to Hole-Transport Layer in Polymeric Light-Emitting Diodes" J. Mater. Chem., 2006, 16, 2387-2394. doi:10.1039/B603704F
  3. ^ F. D. Hager "Triphenylamine" Org. Synth. 1928, 8, 116. doi:10.15227/orgsyn.008.0116