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2,4,6-Trinitroaniline

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2,4,6-Trinitroaniline
Picramide molecule
Names
Preferred IUPAC name 2,4,6-Trinitroaniline
Other names Picramide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.004 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4N4O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H,7H2Key: IAHOUQOWMXVMEH-UHFFFAOYSA-N
  • InChI=1/C6H4N4O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H,7H2Key: IAHOUQOWMXVMEH-UHFFFAOYAP
SMILES
  • c1c(cc(c(c1(=O))N)(=O))(=O)
Properties
Chemical formula C6H4N4O6
Molar mass 228.12 g/mol
Appearance yellow/orange/red powder
Density 1.8 g/cm
Melting point 188 °C (370 °F; 461 K)
Boiling point explodes before boiling
Solubility in water insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards instantaneous explosion
Flash point unknown
Autoignition
temperature 		unknown
Explosive data
Shock sensitivity unknown
Friction sensitivity unknown
Detonation velocity 7,300 m/s
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2,4,6-Trinitroaniline, C6H4N4O6, abbreviated as TNA and also known as picramide, a nitrated amine. Materials in this group range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. The appearance of trinitroaniline varies from yellow to orange to red depending on its purity and concentration.

Applications

Trinitroaniline is only used in modern times in the small warheads of some explosive devices such as mortars. In World War II it was used by Imperial Japanese Navy as Type 97 bakuyaku (Model 1931 explosive) in some versions of gun projectiles instead of less stable burster schimose (picric acid). It was also used in the Yokosuka MXY-7 Ohka, a kamikaze antishipping human-guided rocket aircraft.

Health and safety

Trinitroaniline is dangerously explosive and also hepatoxic. Symptoms of exposure to this compound may include skin and eye irritation, headache, drowsiness, weakness, cyanosis, and respiratory distress.

See also

References

  1. "2,4,6-TRINITROANILINE | CAMEO Chemicals | NOAA".
  2. "Definitions and Information about Naval Guns - NavWeaps".
  3. "2,4,6-Trinitroaniline - Hazardous Agents | Haz-Map". haz-map.com. Retrieved 2024-05-31.
  • Holden, James R.; Dickinson, Charles; Bock, Charles M. (1972). "Crystal structure of 2,4,6-trinitroaniline". The Journal of Physical Chemistry. 76 (24): 3597–3602. doi:10.1021/j100668a017.
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