Pentaerythritol tetranitrate

"PETN" redirects here. For the wind power station, see Taiba N'Diaye Wind Power Station.

Pentaerythritol tetranitrate
Skeletal formula
Ball-and-stick model
Pentaerythritol tetranitrate after crystalization from acetone
Names
Preferred IUPAC name
2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate
Other names
[3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.987 Edit this at Wikidata
UNII
  • InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2 checkY
    Key: TZRXHJWUDPFEEY-UHFFFAOYSA-N checkY
  • InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
  • C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
Properties
C5H8N4O12
Molar mass 316.137 g/mol
Appearance White crystalline solid[1]
Density 1.77 g/cm3 at 20 °C
Melting point 141.3 °C (286.3 °F; 414.4 K)
Boiling point 180 °C (356 °F; 453 K) (decomposes above 150 °C (302 °F))
Explosive data
Shock sensitivity Medium
Friction sensitivity Medium
Detonation velocity 8400 m/s (density 1.7 g/cm3)
RE factor 1.66
Hazards
GHS labelling:
GHS06: Toxic GHS01: Explosive GHS08: Health hazard
Danger
H201, H241, H302, H316, H370, H373
P210, P250, P261, P264, P301+P312, P370+P380, P372, P401, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
1
3
190 °C (374 °F; 463 K)
Pharmacology
C01DA05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA (ПЕНТА, primarily in Russian), TEN (tetraeritrit nitrate), corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66.[2] When mixed with a plasticizer, PETN forms a plastic explosive.[3] Along with RDX it is the main ingredient of Semtex.

PETN is also used as a vasodilator drug to treat certain heart conditions, such as for management of angina.[4][5]

  1. ^ "Provisional Peer-Reviewed Toxicity Values for Pentaerythritol Tetranitrate (PETN) (CASRN 78-11-5)" (PDF). Provisional Peer-Reviewed Toxicity Values. United States Environmental Protection Agency. July 2021. Archived (PDF) from the original on August 1, 2024.
  2. ^ "PETN (Pentaerythritol tetranitrate)". Retrieved March 29, 2010.
  3. ^ Childs, John (1994). "Explosives" (Google Books extract). A dictionary of military history and the art of war. ISBN 978-0-631-16848-5.
  4. ^ "New Drugs". Can Med Assoc J. 80 (12): 997–998. 1959. PMC 1831125. PMID 20325960.
  5. ^ Ebadi, Manuchair S. (1998). CRC desk reference of clinical pharmacology (Google Books excerpt). CRC Press. p. 383. ISBN 978-0-8493-9683-0.