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New Journal of Chemistry
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DOI: 10.1039/C8NJ01341A
COMMUNICATION
Journal Name
(ANTP) starting from 4-amino-2,6-dichloropyridine, followed
by nitration, azidonation, nitrogen elimination and ring
closure, and again azidonation and azido-tetrazolo
tautomerism. ANTP displays a high density (1.92 g/cm3 at 293
K), low thermal stability, and is predicted to be a high
performance energetic material.
Notes and references
1
P. F. Pagoria, G. S. Lee, A. R. Mitchell and R. D. Schmidt,
Thermochimica Acta, 2002, 384, 187.
2
C. Ma, Z. Liu, X. Xu, and Q. Yao, Chinese Journal of Organic
Chemistry, 2014, 34, 1288.
3
4
H. Gao and J. M. Shreeve, Chemical Reviews, 2011, 111, 7377.
Y. Zhang, C. Zhou, B. Wang, Y. Zhou, K. Xu, S. Jia and F. Zhao,
Propellants, Explosives, Pyrotechnics, 2014, 39, 809.
5
6
Bailey A S, and Case J R, Tetrahedron, 1958, 3, 113.
P. Yin, J. Zhang, G. H. Imler, D. A. Parrish and J. M. Shreeve,
Angewandte Chemie International Edition, 2017, 56, 8834.
D. E. Chavez, J. C. Bottaro, M. Petrie and D. A. Parrish,
Angewandte Chemie, 2015, 127, 13165.
C. K. Lowe-Ma, R. A. Nissan and W. S. Wilson, The Journal of
Organic Chemistry, 1990, 55, 3755.
Experimental
7
8
Caution: Some compounds are energetic materials that tend to
explode under certain conditions. Proper protective measures
(work with small quantities, safety glassed, face shields) should be
observed.
10 M. H. V. Huynh, M. A. Hiskey, D. E. Chavez and R. D. Gilardi,
Journal of Energetic Materials, 2005, 23, 99.
11 J. Zhang, S. Dharavath, L. A. Mitchell, D. A. Parrish and J. M.
Shreeve, Journal of the American Chemical Society, 2016, 138
7500.
12 M. J. Frisch, et al. Gaussian 09, Revision D. 01 (Gaussian Inc.,
2009).
13 X. Li, R. Zhang and X. Zhang, Journal of Hazardous Materials,
2010, 183, 622.
General: Melting point was measured on an X-4 melting point
apparatus and was uncorrected. 1H NMR and 13C NMR were
recorded on a Bruker Avance Spectrometer. The coupling constants
(J) were reported in hertz (Hz). High-resolution mass spectra were
recorded on a Finnigan TSQ Quantum ultra AM mass spectrometer.
Elemental analyses were carried out on a Perkin-Elmer instrument.
Thermogravimetry and differential scanning calorimetry (TG-DSC)
analysis was conducted on a Q600SDT.
,
14 D. M. Badgujar, M. B. Talawar, S. N. Asthana and P. P.
Mahulikar, Journal of Hazardous Materials, 2008, 151, 289.
Synthesis of 2. A solution of 4-amino-2,6-dichloropyridine (0.81 g, 5
mmol) in concentrated sulfuric acid (10 mL) was stirred vigorously
at room temperature and treated portionwise with potassium
nitrate (1.52 g, 15 mmol). Then the mixture was heated to 50 for
30 min. After pouring over ice water, the precipitate solid was
filtered, washed with cold water and dried. Yield: yellow solid, 0.88
15
G. H. Tao, B. Twamley and J. M. Shreeve, Journal of
Materials Chemistry, 2009, 19, 5850.
16 P. He, L. Wu, J. Wu, Q. Wang, Z. Li, M. Gozin, and J. Zhang,
Chemistry-A European Journal, 2017, 23, 11159.
17 P. Yin, L. A. Mitchell, D. A. Parrish, and J. M. Shreeve,
Chemistry–An Asian Journal, 2017, 12, 378.
18 Test methods according to the UN Recommendations on the
Transport of Dangerous Goods, Manual of Tests and Criteria,
United Nations Publication, New York, 4th edn, 2003; 13.4.2
g (70%). m.p. 159-161
;
1H NMR (DMSO-d6, 500 MHz):
142.39, 141.03, 132.00; Anal.
δ 8.25 (s,
2H); 13C NMR (DMSO-d6, 125 MHz):
δ
Test 3 (ii) BAM Fall hammer, pp. 75
friction apparatus, pp. 104 107.
–82; 13.5.1 Test 3: BAM
Calcd. for C5H2Cl2N4O4: C, 23.74; H, 0.80; N, 22.14; found: C, 23.65;
–
H, 1.02; N, 22.19%; MS (ESI) m/z: 250.87: 252.86: 254.87= 9: 6: 1
(M-H).
Synthesis of 6.
4-amino-2,6-dichloro-3,5-dinitropyridine (1.26 g,
5 mmol) was
dissolved in acetone (15 mL) and sodium azide (0.98 g, 15 mmol)
was added portionwise at room temperature, then heated up to 30
for another 30 min. The mixture was distilled under reduced
pressure, dissolved with water (15 mL), extracted with ethyl acetate
(2×25 mL), The combined organic layers were dried over MgSO4 and
solvent evaporated. Yield: yellow solid, 1.07 g (90%). Tdec: 150 ; 1H
NMR (DMSO-d6, 400 MHz):
(DMSO-d6, 100 MHz): 148.96, 144.27, 141.87, 111.17, 105.06;
δ
10.17 (s, 1H), 9.50 (s, 1H); 13C NMR
δ
Anal. Calcd. for C5H2N8O4: C, 25.22; H, 0.85; N, 47.06; found: C,
25.10; H, 1.01; N, 47.22%; MS (ESI) m/z: 236.96(M-H).
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This research was supported by National Natural Science
Foundation of China (No. 21436006, 21576136), and
Postdoctoral Science Foundation of Jiangsu Province of China
(No: 1601053B).
4 | New J. Chem., 2018, 00, 1-4
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