Hexanitrobenzene

Hexanitrobenzene

Skeletal formula
Ball-and-stick model
Names
IUPAC name 1,2,3,4,5,6-Hexanitrobenzene
Identifiers
CAS Number	13232-74-1 N
ChemSpider	10445694 Y
Jmol 3D model	Interactive image
PubChem	12488953
InChI InChI=1S/C6N6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18 Y Key: BVKZIAODKDJPLW-UHFFFAOYSA-N Y InChI=1/C6N6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18 Key: BVKZIAODKDJPLW-UHFFFAOYAP
SMILES c1(c(c(c(c(c1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	C6N6O12
Molar mass	348.10 g/mol
Appearance	Yellow or brown powdered crystals
Density	1.985 g/cm3
Melting point	256 to 264 °C (493 to 507 °F; 529 to 537 K)
Vapor pressure	{{{value}}}
Explosive data
Shock sensitivity	None
Friction sensitivity	None
Detonation velocity	9,340 m/s
RE factor	1.8
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Hexanitrobenzene, also known as HNB, is a high-density explosive compound with chemical formula C₆N₆O₁₂, obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid.

Properties

HNB has the undesirable property of being moderately sensitive to light and therefore hard to utilize safely. It is not currently used in any production explosives applications, though it is used as a precursor chemical in one method of production of TATB, another explosive.

HNB was experimentally used as a gas source for explosively pumped gas dynamic laser. In this application, HNB and tetranitromethane are preferred to more conventional explosives because the explosion products CO₂ and N₂ are a simple enough mixture to simulate gas dynamic processes and quite similar to conventional gas dynamic laser medium. The water and hydrogen products of many other explosives could interfere with vibrational states of CO₂ in this type of laser.

Preparation

During World War II a method of synthesis of hexanitrobenzene was suggested in Germany, and the product was supposed to be manufactured on a semi-industrial scale according to the following scheme:

C₆H₃(NO₂)₃ → C₆H₃(NHOH)₃ (partial reduction)

C₆H₃(NHOH)₃ → C₆(NO₂)₃(NHOH)₃ (nitration)

C₆(NO₂)₃(NHOH)₃ → C₆(NO₂)₆ (oxidation)

Complete nitration of benzene is practically impossible, because the nitro groups are deactivating groups for further nitration.

Additional properties

• Chapman-Jouget detonation pressure: 43 GPa
• Crystal Density: 2.01

See also

• ONC
• Tetryl
• TNT
• RE factor

References

• Heats of Formation and Chemical Compositions
• The synthesis and characterisation of halogen and nitro phenyl azide derivatives as highly energetic materials., PhD Thesis, Adam, D; 2001

• Accurate determination of pair potentials for a C_wH_xN_yO_z system of molecules: A semiempirical method, Thiel et al., 1995
• Condensed explosive gas dynamic laser, United States Patent 4099142