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Volumn 49, Issue 18, 2010, Pages 3177-3181

Selective preparation of 3,4,5-Trinitro-1H-Pyrazole: A stable allCarbon-nitrated arene

Author keywords

Explosives; Hazardous materials; Nitration; Nitrogen heterocycles; Synthetic methods

Indexed keywords

1H-PYRAZOLE; ELECTROPHILES; NITRO GROUP; NITROGEN HETEROCYCLES; RING GEOMETRY; SYNTHETIC METHODS;

EID: 77951628575     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000764     Document Type: Article
Times cited : (228)

References (39)
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    • TNP 6 and its derivatives have been patented. Impact, friction, and sparkling tests along with performances have been reported therein: G. Hervé, Pat. US 2009/0186931, 2009, WO 2008/ 152525, 2008; Pat. FR2917409, 2007.
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    • the Supporting Information to find all the safety and performance data
    • See also the Supporting Information to find all the safety and performance data.
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    • For instance, the nitration of 1H-pyrazole leads only to one product, even under severe conditions. After 48 h at 110°C, 4-nitropyrazole is obtained in 80% yield, see: R. Htlttel, F. Büchele. P. Jochum, Chem. Ber. 1955, 88, 1577-1585.
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    • 4-Amino-3,5-dinitropyrazole was claimed to be prepared by alkaline hydrolysis of 3,5-dinitro-4-(methoxycarbonyl)amino-pyrazole, see: I. L. Dalinger, T. I. Cherkasova, S. A. Shevelev, Russ. Chem. Bull. 1993, 42, 1552-1554.
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    • The preparation of 1.3,4-trinitropyrazole was first fully reported in 2007 by us; see ref. [4], Previously, only a brief NMR description had been published elsewhere, see: B. I. Ugrak, V. S. Bogdanov, S. A. Shevelev, I. L. Dalinger, Mendeleev Commun. 1993, 3, 109-110.
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    • An azoxy by-product has been successfully detected by NMR and MS analysis. The other by-products remain unidentified
    • An azoxy by-product has been successfully detected by NMR and MS analysis. The other by-products remain unidentified.
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    • Although the aspect was not satisfactory, all the IR (in KBr) and NMR analyses were rigorously identical to those previously performed on the clean, white solid obtained by oxidation
    • Although the aspect was not satisfactory, all the IR (in KBr) and NMR analyses were rigorously identical to those previously performed on the clean, white solid obtained by oxidation.
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    • 1, this value indicates a low decomposition process under nitrogen atmosphere
    • 1, this value indicates a low decomposition process under nitrogen atmosphere.
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    • The dinitrofurazanyl ether formation can be detected by TLC analysis and subsequent NMR analysis
    • The dinitrofurazanyl ether formation can be detected by TLC analysis and subsequent NMR analysis.
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    • note
    • 2 (2,4,6-trinitro-phenyl-O-hydroxylamine) is thermodynamically favored.
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    • 2).
    • 2).
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    • CCDC 770180 (6), CCDC 770181 (6′), and CCDC 770182 (8) contain the supplementary crystallography data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 770180 (6), CCDC 770181 (6′), and CCDC 770182 (8) contain the supplementary crystallography data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif., www.angewandte.org


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.