2,4,6-Trinitroaniline

2,4,6-Trinitroaniline

Names
Preferred IUPAC name 2,4,6-Trinitroaniline
Other names Picramide
Identifiers
CAS Number	489-98-5 N
3D model (JSmol)	Interactive image
ChemSpider	9852 Y
ECHA InfoCard	100.007.004
PubChem CID	10271
UNII	ZL7CZQ6FZC Y
CompTox Dashboard (EPA)	DTXSID9074850
InChI InChI=1S/C6H4N4O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H,7H2 Y Key: IAHOUQOWMXVMEH-UHFFFAOYSA-N Y InChI=1/C6H4N4O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H,7H2 Key: IAHOUQOWMXVMEH-UHFFFAOYAP
SMILES c1c(cc(c(c1[N+](=O)[O-])N)[N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	C6H4N4O6
Molar mass	228.12 g/mol
Appearance	yellow/orange/red powder
Density	1.8 g/cm3
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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[1] The appearance of trinitroaniline varies from yellow to orange to red depending on its purity and concentration.

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).^[2] It was also used in the Yokosuka MXY-7 Ohka, a kamikaze antishipping human-guided rocket aircraft.

Trinitroaniline is dangerously explosive and also hepatoxic.^[3] Symptoms of exposure to this compound may include skin and eye irritation, headache, drowsiness, weakness, cyanosis, and respiratory distress.^{[medical citation needed]}

• Aniline
• Tetryl

• 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.