N-Vinylcarbazole

N-vinylcarbazole^[1]

Names
IUPAC name 9-ethenyl-9H-carbazole
Other names 9-vinyl-9H-carbazole, NVC
Identifiers
CAS Number	1484-13-5
ChemSpider	14414
EC Number	216-055-0
Jmol interactive 3D	Image
PubChem	15143
RTECS number	FE6350000
InChI InChI=1S/C14H11N/c1-2-15-13-9-5-3-7-11(13)12-8-4-6-10-14(12)15/h2-10H,1H2
SMILES c1cccc3c1c2c(cccc2)n3C=C
Properties
Chemical formula	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]
Solubility in water	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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Infobox references

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 compound is used in the photoreceptors of photocopiers.^[4] Upon exposure to γ-irradiation, N-vinylcarbazole undergoes solid-state polymerisation.^[5]

Synthesis

One possible synthesis, patented by Nippon Shokubai, is based on the reaction of carbazole with ethylene carbonate at 300 °C (572 °F)-500 °C (932 °F) under partial vacuum and in the presence of alkaline earth metal and alkaline metal catalyst and silica. This reaction produces N-(2-Hydroxyethyl) carbazole, which in turn generates vinylcarbazole through water eliminiation.^[3]

Related compounds

• Carbazole

References

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. Sigma-Aldrich 9-Vinylcarbazole product page
3. Conti, Francsco (June 2006). "Nuova via di sintesi del vinilcarbazolo". La Chimica e l'Industria (in Italian) (Società Chimica Italiana) (5): 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.