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Communication
Selective Preparation of 3,4,5-Trinitro-1H-Pyrazole: A Stable All-Carbon-Nitrated Arene
Article first published online: 26 MAR 2010
DOI: 10.1002/anie.201000764
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1521-3773/asset/cover.gif?v=1&s=412bc65bdcb3f0e34a94f27c1c13e908726694d4 "Angewandte Chemie International Edition")
Additional Information
How to Cite
Hervé, G., Roussel, C. and Graindorge, H. (2010), Selective Preparation of 3,4,5-Trinitro-1H-Pyrazole: A Stable All-Carbon-Nitrated Arene. Angew. Chem. Int. Ed., 49: 3177–3181. doi: 10.1002/anie.201000764
Publication History
- Issue published online: 9 APR 2010
- Article first published online: 26 MAR 2010
- Manuscript Received: 29 DEC 2009
Keywords:
- explosives;
- hazardous materials;
- nitration;
- nitrogen heterocycles;
- synthetic methods
Lowering the boom: 3,4,5-trinitro-1H-pyrazole (TNP, see picture) has been prepared by the unexpected nitration of 3,5-dinitropyrazole with a super-electrophile generated from 20–30 % sulfuric oleum mixed with nitric acid. The remarkable stability of TNP results from the preservation of the ring geometry and the specific conformation of the nitro group at C4 which confers low acidity on the material.