Xylitol pentanitrate

Xylitol pentanitrate
Names
IUPAC name
1,2,3,4,5-Pentakis-nitrooxy-pentane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H7N5O15/c11-6(12)21-1-3(23-8(15)16)5(25-10(19)20)4(24-9(17)18)2-22-7(13)14/h3-5H,1-2H2/t3-,4+,5+ ☒N
    Key: STNMPEICBMBFAP-SCDXWVJYSA-N ☒N
  • InChI=1/C5H7N5O15/c11-6(12)21-1-3(23-8(15)16)5(25-10(19)20)4(24-9(17)18)2-22-7(13)14/h3-5H,1-2H2/t3-,4+,5+
    Key: STNMPEICBMBFAP-SCDXWVJYBV
  • C([C@H]([C@@H]([C@H](CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
Properties
C5H7N5O15
Molar mass 377.131 g·mol−1
Density 1.852 g/cm3
Melting point 45.5 °C (114 °F; 318 K)
Boiling point 163-185 °C (346 - 358 °F; 436 - 458 K) (Decomposes)
Solubility Soluble in ethanol, toluene, chloroform, acetone[1]
log P 3.42[2]
Structure
Monoclinic [3]
Explosive data
Shock sensitivity 4.5 J[3]
Friction sensitivity 18 N [3]
Detonation velocity 7,100 m/s
Hazards
GHS labelling:
GHS01: Explosive GHS03: Oxidizing
167 °C (333 °F; 440 K) [3]
Lethal dose or concentration (LD, LC):
148 μM (in splenocytes)[2]
Related compounds
Related compounds
 Xylitol
Erythritol tetranitrate
Pentaerythritol tetranitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Xylitol pentanitrate (XPN) is a nitrated ester primary explosive[3][4] first synthesized in 1891 by Gabriel Bertrand.[5][6] Law enforcement has taken an interest in XPN along with erythritol tetranitrate (ETN) and pentaerythritol tetranitrate (PETN) due to their ease of synthesis, which makes them accessible to amateur chemists and terrorists.[7][8]

  1. ^ Stark, Kelly-Anne S.; Gascooke, Jason R.; Gibson, Christopher T.; Lenehan, Claire E.; Bonnar, Callum; Fitzgerald, Mark; Kirkbride, K. Paul (November 2020). "Xylitol pentanitrate – Its characterization and analysis". Forensic Science International. 316: 110472. doi:10.1016/j.forsciint.2020.110472. PMID 32919164. S2CID 221643415.
  2. ^ a b Šarlauskas, Jonas; KrikŠtopaitis, Kastis; MiliukienĖ, Valė; ČĖnas, Narimantas; AnuseviČius, Žilvinas; ŠaikŪnas, Algirdas (2011). "Investigation on the Electrochemistry and Cytotoxicity of Organic Nitrates and Nitroamines". Central European Journal of Energetic Materials. 8: 15–24.
  3. ^ a b c d e Stark, Kelly-Anne S.; Alvino, Jason F.; Kirkbride, K. Paul; Sumby, Christopher J.; Metha, Gregory F.; Lenehan, Claire E.; Fitzgerald, Mark; Wall, Craig; Mitchell, Mark; Prior, Chad (2019). "Crystal Structure, Sensitiveness and Theoretical Explosive Performance of Xylitol Pentanitrate (XPN)". Propellants, Explosives, Pyrotechnics. 44 (5): 541–549. doi:10.1002/prep.201800337. ISSN 0721-3115. S2CID 109872121.
  4. ^ Klapötke, Thomas M. (2021-01-18). "X". O-Z. De Gruyter. pp. 2027–2030. doi:10.1515/9783110672558-019. ISBN 978-3-11-067255-8.
  5. ^ Wright, I. G.; Hayward, L. D. (1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN 0008-4042.
  6. ^ Bertrand, G. (20 May 1891). "Sur la constitution de la xylite et du xylose". Bulletin de la Société chimique de Paris (in French). V (10). Paris: L. Hachette: 740.
  7. ^ Yan, Qi-Long; Künzel, Martin; Zeman, Svatopluk; Svoboda, Roman; Bartošková, Monika (2013). "The effect of molecular structure on thermal stability, decomposition kinetics and reaction models of nitric esters". Thermochimica Acta. 566: 137–148. Bibcode:2013TcAc..566..137Y. doi:10.1016/j.tca.2013.05.032.
  8. ^ Dong, Jun; Yan, Qi-Long; Liu, Pei-Jin; He, Wei; Qi, Xiao-Fei; Zeman, Svatopluk (2018). "The correlations among detonation velocity, heat of combustion, thermal stability and decomposition kinetics of nitric esters". Journal of Thermal Analysis and Calorimetry. 131 (2): 1391–1403. doi:10.1007/s10973-017-6706-5. ISSN 1388-6150. S2CID 102678177.