N-Vinylcarbazole

N-vinylcarbazole[1]
Names
Preferred IUPAC name
9-Ethenyl-9H-carbazole
Other names
9-Vinyl-9H-carbazole, NVC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.596 Edit this at Wikidata
EC Number
  • 216-055-0
RTECS number
  • FE6350000
UNII
  • InChI=1S/C14H11N/c1-2-15-13-9-5-3-7-11(13)12-8-4-6-10-14(12)15/h2-10H,1H2
    Key: KKFHAJHLJHVUDM-UHFFFAOYSA-N
  • c1cccc3c1c2c(cccc2)n3C=C
Properties
C14H11N
Molar mass 193.244 g⋅mol−1
Appearance Pale brown crystalline solid[2]
Melting point 66 °C (151 °F; 339 K)
Boiling point 154 to 155 °C (309 to 311 °F; 427 to 428 K) 3 mmHg[2]
Insoluble
Solubility in diethyl ether Very soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Vinylcarbazole is an organic compound used as a monomer in the production of poly(vinylcarbazole),[3] a conductive polymer, in which conductivity is photon-dependent. The benzine compound is used in the photoreceptors of photocopiers.[4] Upon exposure to γ-irradiation, N-vinylcarbazole undergoes solid-state polymerisation.[5]

It is produced by the vinylation of carbazole with acetylene in the presence of base.[6]

  1. ^ Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–518. ISBN 978-0-8493-0488-0.
  2. ^ a b Sigma-Aldrich 9-Vinylcarbazole product page
  3. ^ Conti, Francsco (June 2006). "Nuova via di sintesi del vinilcarbazolo". La Chimica & L'Industria (in Italian) (5). Società Chimica Italiana: 82.
  4. ^ G. Burton; J. Holman; J. Lazonby; G. Pilling; D. Waddington (2000). Chemical Storylines (2nd ed.). Heinemann Educational Publishers. pp. 121–122. ISBN 0-435-63119-5.
  5. ^ K. Tsutsui; K. Hirotsu; M. Umesaki; M. Kurahashi; A. Shimada; T. Higuchi (1976). "Structural chemistry of polymerizable monomers. I. Crystal structure of N-vinylcarbazole". Acta Crystallogr. B. 32: 3049–3053. doi:10.1107/S0567740876009527.
  6. ^ Pässler, Peter; Hefner, Werner; Buckl, Klaus; Meinass, Helmut; Meiswinkel, Andreas; Wernicke, Hans-Jürgen; Ebersberg, Günter; Müller, Richard; Bässler, Jürgen; Behringer, Hartmut; Mayer, Dieter (2008). "Acetylene Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_097.pub3. ISBN 3527306730.