Benzotrifuroxan

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Benzotrifuroxan
Benzotrifuroxan structure.svg
Names
Other names
Benzenetrifuroxan
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C6N6O6/c13-10-4-1(7-16-10)5-3(8-17-11(5)14)6-2(4)9-18-12(6)15
    Key: ROSQKRBIBODSRH-UHFFFAOYSA-N
  • C12=NO[N+](=C1C3=NO[N+](=C3C4=NO[N+](=C24)[O-])[O-])[O-]
Properties
C6N6O6
Molar mass 252.102 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benzotrifuroxan is a heterocyclic organic compound that is related to 1,2,5-oxadioles. The high-energy compound is explosive.

Contents

History

The compound was first synthesized in 1924 by O. Turek as hexanitrosobenzene. [1] [2] In addition to the hexanitroso structure, symmetric polycyclic structures could also be formulated. [3] [4]

Historical, non-real structures of benzotrifuroxan Benzotrifuroxan non-real structures.svg
Historical, non-real structures of benzotrifuroxan

Characteristics

Physical properties

Benzotrifuroxan is a crystalline solid that melts at 195 °C. [5]  The compound crystallizes in an orthorhombic crystal lattice with the space group Pna21. [4] [6]  The molar enthalpy of formation is 606 kJ·mol−1, the enthalpy of combustion is −2967 kJ·mol−1. [7]

Chemical properties

Benzotrifuroxan can decompose explosively. The heat of explosion is 5903 kJ·kg −1, [8] the detonation speed is 8.61 km·s −1. [9]  The compound is sensitive to impact. [10]

Benzotrifuroxan forms stable complexes with aromatic hydrocarbons such as naphthalene, 1-phenylnaphthalene, 2-phenylnaphthalene and tetrahydronaphthalene. Recrystallization in benzene yields a 1:1 complex with the solvent, whereby the benzene can only be removed at 100 °C in vacuum. [11]

Synthesis

Benzotrifuroxan can be obtained by thermal degradation of 1,3,5-triazido-2,4,6-trinitrobenzene. [1] [2]

1,3,5-Triazido-2,4,6-trinitrobenzene decomposition.svg

A further synthesis can be carried out by reacting 5,7-dichloro-4,6-dinitronbenzofuroxan with sodium azide. [12]

Uses

In combination with TNT, the compound can be used to produce nanodiamonds using detonation shock waves. [13]

Related Research Articles

<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">Hexanitrobenzene</span> Chemical compound

Hexanitrobenzene, also known as HNB, is a nitrobenzene compound in which six nitro groups are bonded to all six positions of a central benzene ring. It is a high-density explosive compound with chemical formula C6N6O12, obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid.

<span class="mw-page-title-main">Silver fulminate</span> High explosive used in bang snaps

Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.

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

Sodium azide is an inorganic compound with the formula NaN3. This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is an ionic substance, is highly soluble in water, and is acutely poisonous.

In chemistry, water(s) of crystallization or water(s) of hydration are water molecules that are present inside crystals. Water is often incorporated in the formation of crystals from aqueous solutions. In some contexts, water of crystallization is the total mass of water in a substance at a given temperature and is mostly present in a definite (stoichiometric) ratio. Classically, "water of crystallization" refers to water that is found in the crystalline framework of a metal complex or a salt, which is not directly bonded to the metal cation.

<span class="mw-page-title-main">Silver perchlorate</span> Chemical compound

Silver perchlorate is the chemical compound with the formula AgClO4. This white solid forms a monohydrate and is mildly deliquescent. It is a useful source of the Ag+ ion, although the presence of perchlorate presents risks. It is used as a catalyst in organic chemistry.

The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry:

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

TATB, triaminotrinitrobenzene or 2,4,6-triamino-1,3,5-trinitrobenzene is an aromatic explosive, based on the basic six-carbon benzene ring structure with three nitro functional groups (NO2) and three amine (NH2) groups attached, alternating around the ring.

<span class="mw-page-title-main">Tetrasulfur tetranitride</span> Chemical compound

Tetrasulfur tetranitride is an inorganic compound with the formula S4N4. This vivid orange, opaque, crystalline explosive is the most important binary sulfur nitride, which are compounds that contain only the elements sulfur and nitrogen. It is a precursor to many S-N compounds and has attracted wide interest for its unusual structure and bonding.

<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).

<span class="mw-page-title-main">2,4,6-Tris(trinitromethyl)-1,3,5-triazine</span> Chemical compound

2,4,6-Tris(trinitromethyl)-1,3,5-triazine is a chemical compound that is a derivative of triazine first prepared in 1995. 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.

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

Silver azide is the chemical compound with the formula AgN3. It is a silver(I) salt of hydrazoic acid. It forms a colorless crystals. Like most azides, it is a primary explosive.

<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the organic derivativess of any group 2 element. It is a subtheme to main group organometallic chemistry. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organometallic group 2 compounds are typically limited to academic interests.

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

Ammonium azide is the chemical compound with the formula [NH4]N3, being the salt of ammonia and hydrazoic acid. Like other inorganic azides, this colourless crystalline salt is a powerful explosive, although it has a remarkably low sensitivity. [NH4]N3 is physiologically active and inhalation of small amounts causes headaches and palpitations. It was first obtained by Theodor Curtius in 1890, along with other azides.

<span class="mw-page-title-main">Silicon tetraazide</span> Chemical compound

Silicon tetraazide is a thermally unstable binary compound of silicon and nitrogen with a nitrogen content of 85.7%. This high-energy compound combusts spontaneously and can only be studied in a solution. A further coordination to a six-fold coordinated structure such as a hexaazidosilicate ion [Si(N3)6]2− or as an adduct with bidentate ligands Si(N3)4·L2 will result in relatively stable, crystalline solids that can be handled at room temperature.

<span class="mw-page-title-main">Cyanuric triazide</span> Chemical compound

Cyanuric triazide (C3N12 or (NCN3)3) is described as an environmentally friendly, low toxicity, and organic primary explosive with a detonation velocity of about 7,300 m s−1 and a autoignition temperature of 205 °C.

Hydrazinium azide or hydrazine azide is a chemical compound with formula H
5N
5 or [N
2H+
5][N−
3]. It is a salt of the hydrazinium cation N
2H+
5 and the azide anion N−
3. It can be seen as a derivative of hydrazine N
2H
4 and hydrazoic acid HN
3. It is an unstable solid.

<span class="mw-page-title-main">(Benzene)ruthenium dichloride dimer</span> Chemical compound

(Benzene)ruthenium dichloride dimer is the organoruthenium compound with the formula [(C6H6)RuCl2]2. This red-coloured, diamagnetic solid is a reagent in organometallic chemistry and homogeneous catalysis.

<span class="mw-page-title-main">Boron triazide</span> Chemical compound

Boron triazide, also known as triazidoborane, is a thermally unstable compound of boron and nitrogen with a nitrogen content of 92.1 %. Formally, it is the triazido derivative of borane and is a covalent inorganic azide. The high-energy compound, which has the propensity to undergo spontaneous explosive decomposition, was first described in 1954 by Egon Wiberg and Horst Michaud of the University of Munich.

References

  1. 1 2 O. Turek: Le 2,4,6-trinitro-1,3,5-triazido-benzene, nouvel explosif d’amorcage. In: Chimie et industrie. Band 26, 1931, S. 781–794.
  2. 1 2 O. Turek: 1,3,5-Triazido-2,4,6-trinitrobenzen, nova inicialna vybusina. In: Chemicky obzor. Nr. 7, 1932, S. 76–79; 97–104.
  3. ↑ Bacon, Neville; Boulton, A. J.; Katritzky, A. R. (1967). "Structure of "hexanitrosobenzene" from vibrational spectroscopy". Trans. Faraday Soc. 63: 833–835. doi:10.1039/TF9676300833.
  4. 1 2 Cady, H. H.; Larson, A. C.; Cromer, D. T. (1 March 1966). "The crystal structure of benzotrifuroxan (hexanitrosobenzene)". Acta Crystallographica. 20 (3): 336–341. Bibcode:1966AcCry..20..336C. doi:10.1107/S0365110X6600080X.
  5. ↑ Boeyens, J. C. A.; Herbstein, F. H. (July 1965). "Molecular Compounds and Complexes. II. Exploratory Crystallographic Study of Some Donor-Acceptor Molecular Compounds 1". The Journal of Physical Chemistry. 69 (7): 2153–2159. doi:10.1021/j100891a003.
  6. ↑ Maslen, E. N. (1 September 1968). "A phase refinement of the crystal structure of benzotrifuroxan". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 24 (9): 1170–1172. Bibcode:1968AcCrB..24.1170M. doi:10.1107/S0567740868003912.
  7. ↑ Rouse, Prince E. (January 1976). "Enthalpies of formation and calculated detonation properties of some thermally stable explosives". Journal of Chemical & Engineering Data. 21 (1): 16–20. doi:10.1021/je60068a026.
  8. ↑ Rice, Betsy M.; Hare, Jennifer (February 2002). "Predicting heats of detonation using quantum mechanical calculations". Thermochimica Acta. 384 (1–2): 377–391. Bibcode:2002TcAc..384..377R. doi:10.1016/S0040-6031(01)00796-1.
  9. ↑ Muthurajan, H; Sivabalan, R; Talawar, M.B; Asthana, S.N (August 2004). "Computer simulation for prediction of performance and thermodynamic parameters of high energy materials". Journal of Hazardous Materials. 112 (1–2): 17–33. Bibcode:2004JHzM..112...17M. doi:10.1016/j.jhazmat.2004.04.012. PMID   15225927.
  10. ↑ Pepekin, V. I.; Korsunskii, B. L.; Denisaev, A. A. (September 2008). "Initiation of solid explosives by mechanical impact". Combustion, Explosion, and Shock Waves. 44 (5): 586–590. Bibcode:2008CESW...44..586P. doi:10.1007/s10573-008-0089-7.
  11. ↑ Bailey, A.S.; Case, J.R. (January 1958). "4:6-dinitrobenzofuroxan, nitrobenzodifuroxan and benzotrifuroxan: A new series of complex-forming reagents for aromatic hydrocarbons". Tetrahedron. 3 (2): 113–131. doi:10.1016/0040-4020(58)80003-4.
  12. ↑ Chugunova, Elena A.; Timasheva, Rezeda E.; Gibadullina, Elmira M.; Burilov, Alexander R.; Goumont, Regis (August 2012). "First Synthesis of Benzotrifuroxan at Low Temperature: Unexpected Behavior of 5,7-Dichloro-4,6-dinitrobenzo-furoxan with Sodium Azide". Propellants, Explosives, Pyrotechnics. 37 (4): 390–392. doi:10.1002/prep.201200080.
  13. ↑ Kozyrev, N. V. (November 2008). "Using the tracer method to study detonation processes". Combustion, Explosion, and Shock Waves. 44 (6): 698–703. Bibcode:2008CESW...44..698K. doi:10.1007/s10573-008-0105-y.

attribution translated from the German article de:Benzotrifuroxan

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