Pentrite

Pentaerythritol tetranitrate

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
CAS Number	78-11-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL466659 Y
ChemSpider	6271 Y
ECHA InfoCard	100.000.987
PubChem CID	6518
InChI 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 Y Key: TZRXHJWUDPFEEY-UHFFFAOYSA-N Y 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
SMILES C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
Properties
Chemical formula	C5H8N4O12
Molar mass	316.137
Appearance	White crystalline solid
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 pictograms
GHS signal word	Danger
GHS hazard statements	H201, H302, H316, H370, H373, H241
GHS precautionary statements	P210, P250, P261, P264, P301+312, P372, P401, P501, P370+380
NFPA 704	1 2 2
Autoignition temperature	190 °C (374 °F; 463 K)
Pharmacology
ATC code	C01DA05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, TEN, corpent, penthrite (or—rarely and primarily in German—as nitropenta), 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 one of the most powerful explosive materials known, with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. 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.

Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer Rheinisch-Westfälische Sprengstoff A.G. of Cologne, Germany. The production of PETN started in 1912, when the improved method of production was patented by the German government. PETN was used by the German Military in World War I. It was also used in the MG FF/M autocannons and many other weapon systems of the Luftwaffe in World War II, specifically in the high explosive "Minengeschoß" shell.

PETN is practically insoluble in water (0.01 g/100 ml at 50 °C), weakly soluble in common nonpolar solvents such as aliphatic hydrocarbons (like gasoline) or tetrachloromethane, but soluble in some other organic solvents, particularly in acetone (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) and dimethylformamide (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). PETN forms eutectic mixtures with some liquid or molten aromatic nitro compounds, e.g. trinitrotoluene (TNT) or tetryl. Due to its highly symmetrical structure, PETN is resistant to attack by many chemical reagents; it does not hydrolyze in water at room temperature or in weaker alkaline aqueous solutions. Water at 100 °C or above causes hydrolysis to dinitrate; presence of 0.1% nitric acid accelerates the reaction.