2,4,6-Tris(trinitromethyl)-1,3,5-triazine

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2,4,6-Tris(trinitromethyl)-1,3,5-triazine
TTNMTZ.svg
2,4,6-Tris(trinitromethyl)-1,3,5-triazine-3D-balls.png
Names
Preferred IUPAC name
Tris(trinitromethyl)-1,3,5-triazine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C6N12O18/c19-10(20)4(11(21)22,12(23)24)1-7-2(5(13(25)26,14(27)28)15(29)30)9-3(8-1)6(16(31)32,17(33)34)18(35)36 Yes check.svgY
    Key: MTNISTQLDNOGTM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6N12O18/c19-10(20)4(11(21)22,12(23)24)1-7-2(5(13(25)26,14(27)28)15(29)30)9-3(8-1)6(16(31)32,17(33)34)18(35)36
    Key: MTNISTQLDNOGTM-UHFFFAOYAO
  • O=[N+]([O-])C(c1nc(nc(n1)C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O)C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O
Properties
C6N12O18
Molar mass 528.132 g·mol−1
Density 1.91 g/cm3
Melting point 91 to 92 °C (196 to 198 °F; 364 to 365 K)
Related compounds
Related compounds
4,4’-Dinitro-3,3’-diazenofuroxan
Cyanuric triazide
Hexanitrohexaazaisowurtzitane
Octanitrocubane
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-Tris(trinitromethyl)-1,3,5-triazine is a chemical compound that is a derivative of triazine first prepared in 1995. [1] It is synthesized by destructive nitration of 2,4,6-tricarboxyl-1,3,5-triazine. It is noteworthy for having more nitro groups than it does carbon atoms, thus potentially being useful as an oxygen source, or added to oxygen-poor explosives to increase their power.

Derivatives have been prepared by nucleophilic displacement of the nitro groups with azide and hydrazine. [2]

Related Research Articles

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In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)–. The simplest ketone is acetone, with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Nitrogen</span> Chemical element, symbol N and atomic number 7

Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element bond to form N2, a colorless and odorless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant uncombined element. Nitrogen occurs in all organisms, primarily in amino acids (and thus proteins), in the nucleic acids (DNA and RNA) and in the energy transfer molecule adenosine triphosphate. The human body contains about 3% nitrogen by mass, the fourth most abundant element in the body after oxygen, carbon, and hydrogen. The nitrogen cycle describes the movement of the element from the air, into the biosphere and organic compounds, then back into the atmosphere.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

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In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases.

<span class="mw-page-title-main">Hydrazine</span> Colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. It is not dissimilar to Diazene or Triazene and, although its name might suggest otherwise, very dissimilar to Triazine and Tetrazine.

<span class="mw-page-title-main">Amino sugar</span>

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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.

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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).

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Hydrazines (R2N−NR2) are a class of chemical compounds with two nitrogen atoms linked via a covalent bond and which carry from one up to four alkyl or aryl substituents. Hydrazines can be considered as derivatives of the inorganic hydrazine (H2N−NH2), in which one or more hydrogen atoms have been replaced by hydrocarbon groups.

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The Stieglitz rearrangement is a rearrangement reaction in organic chemistry which is named after the American chemist Julius Stieglitz (1867–1937) and was first investigated by him and Paul Nicholas Leech in 1913. It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines. It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift. As an example, triaryl hydroxylamines can undergo a Stieglitz rearrangement by dehydration and the shift of a phenyl group after activation with phosphorus pentachloride to yield the respective triaryl imine, a Schiff base.

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<span class="mw-page-title-main">4-Chlorophenyl azide</span> Chemical compound

4-Chlorophenyl azide is an organic aryl azide compound with the chemical formula C6H4ClN3. The geometry between the nitrogen atoms in the azide functional group is approximately linear while the geometry between the nitrogen and the carbon of the benzene is trigonal planar.

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An organic azide is an organic compound that contains an azide functional group. Because of the hazards associated with their use, few azides are used commercially although they exhibit interesting reactivity for researchers. Low molecular weight azides are considered especially hazardous and are avoided. In the research laboratory, azides are precursors to amines. They are also popular for their participation in the "click reaction" and in Staudinger ligation. These two reactions are generally quite reliable, lending themselves to combinatorial chemistry.

References

  1. Shastin AV, Godovikova TI, Golova SP, Kuz'min VS, Khmel'nitskii LI, Korsunskii BL (1995). "Synthesis of 2,4,6-Tris(trinitromethyl)-1,3,5-triazine". Mendeleev Communications. 5: 17–18. doi:10.1070/MC1995v005n01ABEH000440.
  2. Shastin AV, Godovikova TI, Korsunskii BL (2003). "Nucleophilic Substitution Reactions of 2,4,6-Tris(trinitromethyl)-1,3,5-triazine. 3. Reaction of 2,4,6-Tris(trinitromethyl)-1,3,5-triazine with Azides and Hydrazine". Chemistry of Heterocyclic Compounds. 39 (3): 354–356. doi:10.1023/A:1023970928207. S2CID   106383383.