2,4,6-Trinitroaniline

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2,4,6-Trinitroaniline
Trinitroaniline structure.svg
2,4,6-Trinitroaniline-3D-balls.png
Names
Preferred IUPAC name
2,4,6-Trinitroaniline
Other names
Picramide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.004 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H4N4O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H,7H2 Yes check.svgY
    Key: IAHOUQOWMXVMEH-UHFFFAOYSA-N Yes check.svgY
  • 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
  • c1c(cc(c(c1[N+](=O)[O-])N)[N+](=O)[O-])[N+](=O)[O-]
Properties
C6H4N4O6
Molar mass 228.12 g/mol
Appearanceyellow/orange/red powder
Density 1.8 g/cm3
Melting point 188 °C (370 °F; 461 K)
Boiling point explodes before boiling
insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
instantaneous explosion
Flash point unknown
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).
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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.

Contents

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). [2] 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. [3] Symptoms of exposure to this compound may include skin and eye irritation, headache, drowsiness, weakness, cyanosis, and respiratory distress.[ medical citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Aromatic compound</span> Compound containing rings with delocalized pi electrons

Aromatic compounds or arenes usually refers to organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's Rule. Aromatic compounds have the following general properties:

<span class="mw-page-title-main">TNT</span> Impact-resistant high explosive

Trinitrotoluene, more commonly known as TNT (and more specifically 2,4,6-trinitrotoluene), and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.

<span class="mw-page-title-main">Lead styphnate</span> Chemical compound

Lead styphnate (lead 2,4,6-trinitroresorcinate, C6HN3O8Pb ), whose name is derived from styphnic acid, is an explosive used as a component in primer and detonator mixtures for less sensitive secondary explosives. Lead styphnate is only slightly soluble in water and methanol. Samples of lead styphnate vary in color from yellow to gold, orange, reddish-brown, to brown. Lead styphnate is known in various polymorphs, hydrates, and basic salts. Normal lead styphnate monohydrate, monobasic lead styphnate, tribasic lead styphnate dihydrate, and pentabasic lead styphnate dehydrate as well as α, β polymorphs of lead styphnate exist.

<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a molecule

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

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<span class="mw-page-title-main">Sodium sulfide</span> Chemical compound

Sodium sulfide is a chemical compound with the formula Na2S, or more commonly its hydrate Na2S·9H2O. Both the anhydrous and the hydrated salts in pure crystalline form are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red owing to the presence of polysulfides and commonly supplied as a crystalline mass, in flake form, or as a fused solid. They are water-soluble, giving strongly alkaline solutions. When exposed to moisture, Na2S immediately hydrates to give sodium hydrosulfide.

<span class="mw-page-title-main">1,3,5-Triazido-2,4,6-trinitrobenzene</span> Chemical compound

1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N3) and three nitro groups (-NO2) alternating around the ring, giving the chemical formula C6(N3)3(NO2)3. Its detonation velocity is 7,350 meters per second, which is comparable to TATB (triaminotrinitrobenzene).

Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.

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<span class="mw-page-title-main">Picryl chloride</span> Chemical compound

Picryl chloride is an organic compound with the formula ClC6H2(NO2)3. It is a bright yellow solid that is highly explosive, as is typical for polynitro aromatics such as picric acid. Its detonation velocity is 7,200 m/s.

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<span class="mw-page-title-main">2,4,6-Trimethylaniline</span> Chemical compound

2,4,6-Trimethylaniline is an organic compound with formula (CH3)3C6H2NH2. It is an aromatic amine that is of commercial interest as a precursor to dyes. It is prepared by selective nitration of mesitylene, avoiding oxidation of the methyl groups, followed by reduction of the resulting nitro group to the aniline.

<span class="mw-page-title-main">1,3,5-Trinitrobenzene</span> Chemical compound

1,3,5-Trinitrobenzene is one of three isomers of trinitrobenzene with the formula C6H3(NO2)3. A pale yellow solid, the compound is highly explosive.

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<span class="mw-page-title-main">2,4,6-Trinitrobenzenesulfonic acid</span> Chemical compound

Trinitrobenzenesulfonic acid (C6H3N3O9S) is a nitroaryl oxidizing acid. Due to its extreme oxidative properties, if mixed with reducing agents including hydrides, sulfides, and nitrides, it may begin a vigorous reaction that culminates in almost immediate 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 because of the explosive tendencies of aromatic nitro compounds which increase in the presence of multiple nitro groups. Not much is known about this compound, but it is used as a peptide terminal amino group neutralizer and is currently being investigated for its effects on the immune system.

2,4-Dinitroaniline is a chemical compound with a formula of C6H5N3O4. It is used as an explosive and as a reagent to detect and characterize aldehydes and ketones.

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.