Synlett 2013; 24(2): 246-248
DOI: 10.1055/s-0032-1317696
letter
© Georg Thieme Verlag Stuttgart · New York

Scalable Synthesis of Pure and Stable Hexaaminobenzene Trihydrochloride

Javeed Mahmood
Interdisciplinary School of Green Energy/Low-Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), 100 Banyeon, Ulsan, 689-798, South Korea   Fax: +82(52)2172019   Email: jbbaek@unist.ac.kr   Email: mslah@unist.ac.kr
,
Dongwook Kim
Interdisciplinary School of Green Energy/Low-Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), 100 Banyeon, Ulsan, 689-798, South Korea   Fax: +82(52)2172019   Email: jbbaek@unist.ac.kr   Email: mslah@unist.ac.kr
,
In-Yup Jeon
Interdisciplinary School of Green Energy/Low-Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), 100 Banyeon, Ulsan, 689-798, South Korea   Fax: +82(52)2172019   Email: jbbaek@unist.ac.kr   Email: mslah@unist.ac.kr
,
Myoung Soo Lah*
Interdisciplinary School of Green Energy/Low-Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), 100 Banyeon, Ulsan, 689-798, South Korea   Fax: +82(52)2172019   Email: jbbaek@unist.ac.kr   Email: mslah@unist.ac.kr
,
Jong-Beom Baek*
Interdisciplinary School of Green Energy/Low-Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), 100 Banyeon, Ulsan, 689-798, South Korea   Fax: +82(52)2172019   Email: jbbaek@unist.ac.kr   Email: mslah@unist.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 04 October 2012

Accepted: 02 November 2012

Publication Date:
04 December 2012 (online)


Abstract

Synthesis of hexaaminobenzene (HAB) in pure and stable form has remained as an important challenge for a long time, since it is a fascinating synthon for the synthesis of aromatic nitrogenous compounds having many interesting applications. Here, we report an improved synthesis of pure and stable HAB form using modified catalytic hydrogenation in aqueous acidic medium. The structure of needle-shaped HAB crystals was confirmed by single-crystal X-ray diffraction study. The synthetic protocol could thus be a simple, but efficient for the large-scale synthesis of highly pure and stable HAB.

Supporting Information

 
  • References

  • 1 Rogers DZ. J. Org. Chem. 1986; 51: 3904
  • 2 Kohne B, Praefcke K. Liebigs Ann. Chem. 1985; 522
  • 3 Breslow R, Maslak P, Thomaides JS. J. Am. Chem. Soc. 1984; 106: 6453
  • 4 Khisamutdinov GK, Korolev VL, Kondyukov IZ, Abdrakhmanov IS, Smirnov SP, Fainzilberg AA, Dorokhov VG. Russ. Chem. Bull. 1993; 42: 136
  • 5 Kohne B, Praefcke K, Derz T, Gondro T, Frolow F. Angew. Chem., Int. Ed. Engl. 1986; 25: 650
  • 6 Wolff JJ, Limbach H.-H. Liebigs Ann. Chem. 1991; 691
  • 7 Praefcke K, Kohne B, Korinth F. Liebigs Ann. Chem. 1990; 203
  • 8 Juárez R, Ramos M, Segura JL, Orduna J, Villacampa B, Alicante R. J. Org. Chem. 2010; 75: 7542
  • 9 Ishi-i T, Murakami K.-I, Imai Y, Mataka S. J. Org. Chem. 2006; 71: 5752
  • 10 Ishi-i T, Murakami K.-I, Imai Y, Mataka S. Org. Lett. 2005; 7: 3175
  • 11 Flurscheim B, Holmes EL. J. Chem. Soc. 1929; 330
  • 12 Thomaides J, Maslak P, Breslow R. J. Am. Chem. Soc. 1988; 110: 3970
  • 13 Kohne B, Praefcke K. Liebigs Ann. Chem. 1987; 265
  • 14 You BW, Bo ZW, Zhi HY, Yan S, Hui Q. Chin. J. Energ. Mater. 2011; 19: 142
  • 15 Mitchell AR, Pagoria PF, Schmidt RD. US 5633406, 1997
  • 16 Ong CW, Liao S.-C, Chang TH, Hsu H.-F. Tetrahedron Lett. 2003; 44: 1477
  • 17 Yeh M.-C, Liao S.-C, Chao S.-H, Ong CW. Tetrahedron 2010; 66: 8888
  • 18 Ong CW, Liao S.-C, Chang TH, Hsu H.-F. J. Org. Chem. 2004; 69: 3181
  • 19 Ishi-i T, Hirayama T, Murakami K.-i, Tashiro H, Thiemann T, Kubo K, Mori A, Yamasaki S, Akao T, Tsuboyama A, Mukaide T, Ueno K, Mataka S. Langmuir 2005; 21: 1261
  • 20 Barlow S, Zhang Q, Kaafarani BR, Risko C, Amy F, Chan CK, Domercq B, Starikova ZA, Antipin MY, Timofeeva TV, Kippelen B, Brédas J.-L, Kahn A, Marder SR. Chem.–Eur. J. 2007; 13: 3537
  • 21 Secondo P, Fages F. Org. Lett. 2006; 8: 1311
  • 22 Juárez R, Ramos MM, Segura JL. Tetrahedron Lett. 2007; 48: 8829
  • 23 Ishi-i T, Hirashima R, Tsutsumi N, Amemori S, Matsuki S, Teshima Y, Kuwahara R, Mataka S. J. Org. Chem. 2010; 75: 6858
  • 24 Breslow R, Jaun B, Kluttz RQ, Xia C.-Z. Tetrahedron 1982; 38: 863
  • 25 Zhao Q, Li R.-F, Xing S.-K, Liu X.-M, Hu T.-L, Bu X.-H. Inorg. Chem. 2011; 50: 10041