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| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 448571173
| verifiedrevid = 448571173
| ImageFile = HHTDD_structure.png
| ImageFile = HHTDD.svg
| ImageSize = 150px
| ImageSize = 200px
| IUPACName = 2,6-dioxo-1,3,4,5,7,8-hexanitrodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine
| PIN = 1,3,4,5,7,8-Hexanitrooctahydrodiimidazo[4,5-''b'':4′,5′-''e'']pyrazine-2,6(1''H'',3''H'')-dione
| OtherNames = Hexanitrohexaazatricyclododecanedione <br> DTNGU <br> Naza/Namsorguyl/uryl HnHaza/amTcDglcDuryl
| OtherNames =
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =
| CASNo = 115029-33-9
| PubChem =
| PubChem = 14870237
| SMILES = C12C(N(C3C(N1[N+](=O)[O-])N(C(=O)N3[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])N(C(=O)N2[N+](=O)[O-])[N+](=O)[O-]
| SMILES = C12C(N(C3C(N1[N+](=O)[O-])N(C(=O)N3[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])N(C(=O)N2[N+](=O)[O-])[N+](=O)[O-]
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=6|H=4|N=12|O=14
| Formula = C<sub>6</sub>H<sub>4</sub>N<sub>12</sub>O<sub>14</sub>
| MolarMass = 468.168
| Appearance =
| Appearance =
| Density =
| Density =
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}}
}}


'''HHTDD''' is a powerful but moisture sensitive [[explosive]] compound. It is essentially an open analogue of the cyclic nitroamine cage compounds such as [[CL-20]]. While it is highly explosive, with a [[velocity of detonation]] even higher than that of CL-20, HHTDD readily decomposes in the presence of even trace amounts of water, making it unsuitable for any practical applications.<ref>{{cite journal|doi =10.1021/jo00010a043|title =Facile synthesis and nitration of cis-syn-cis-2,6-dioxodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine|year =1991|last1 =Vedachalam|first1 =Murugappa|last2 =Ramakrishnan|first2 =Vayalakkavoor T.|last3 =Boyer|first3 =Joseph H.|last4 =Dagley|first4 =Ian J.|last5 =Nelson|first5 =Keith A.|last6 =Adolph|first6 =Horst G.|last7 =Gilardi|first7 =Richard|last8 =George|first8 =Clifford|last9 =Flippen-Anderson|first9 =Judith L.|journal =The Journal of Organic Chemistry|volume =56|issue =10|pages =3413–3419}}</ref>
'''HHTDD''' ('''hexanitrohexaazatricyclododecanedione''') is a powerful but moisture sensitive [[explosive]] compound. It is essentially an open analogue of the cyclic nitroamine cage compounds such as [[CL-20]]. While it is highly explosive, with a [[velocity of detonation]] even higher than that of CL-20, HHTDD readily decomposes in the presence of even trace amounts of water, making it unsuitable for any practical applications.<ref>{{cite journal|doi =10.1021/jo00010a043|title =Facile synthesis and nitration of cis-syn-cis-2,6-dioxodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine|year =1991|last1 =Vedachalam|first1 =Murugappa|last2 =Ramakrishnan|first2 =Vayalakkavoor T.|last3 =Boyer|first3 =Joseph H.|last4 =Dagley|first4 =Ian J.|last5 =Nelson|first5 =Keith A.|last6 =Adolph|first6 =Horst G.|last7 =Gilardi|first7 =Richard|last8 =George|first8 =Clifford|last9 =Flippen-Anderson|first9 =Judith L.|journal =The Journal of Organic Chemistry|volume =56|issue =10|pages =3413–3419}}</ref>


==See also==
==See also==
*[[TNGU]]
*[[2,4,6-Tris(trinitromethyl)-1,3,5-triazine]]
*[[2,4,6-Tris(trinitromethyl)-1,3,5-triazine]]
*[[4,4’-Dinitro-3,3’-diazenofuroxan]] (DDF)
*[[4,4’-Dinitro-3,3’-diazenofuroxan]] (DDF)

Latest revision as of 01:44, 25 June 2022

HHTDD
Names
Preferred IUPAC name
1,3,4,5,7,8-Hexanitrooctahydrodiimidazo[4,5-b:4′,5′-e]pyrazine-2,6(1H,3H)-dione
Other names
Hexanitrohexaazatricyclododecanedione
DTNGU
Naza/Namsorguyl/uryl HnHaza/amTcDglcDuryl
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H4N12O14/c19-5-9(15(25)26)1-2(10(5)16(27)28)8(14(23)24)4-3(7(1)13(21)22)11(17(29)30)6(20)12(4)18(31)32/h1-4H checkY
    Key: ZFBXJPJQJKATGM-UHFFFAOYSA-N checkY
  • InChI=1/C6H4N12O14/c19-5-9(15(25)26)1-2(10(5)16(27)28)8(14(23)24)4-3(7(1)13(21)22)11(17(29)30)6(20)12(4)18(31)32/h1-4H
    Key: ZFBXJPJQJKATGM-UHFFFAOYAE
  • C12C(N(C3C(N1[N+](=O)[O-])N(C(=O)N3[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])N(C(=O)N2[N+](=O)[O-])[N+](=O)[O-]
Properties
C6H4N12O14
Molar mass 468.168 g·mol−1
Explosive data
Detonation velocity 9700 m/s
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

HHTDD (hexanitrohexaazatricyclododecanedione) is a powerful but moisture sensitive explosive compound. It is essentially an open analogue of the cyclic nitroamine cage compounds such as CL-20. While it is highly explosive, with a velocity of detonation even higher than that of CL-20, HHTDD readily decomposes in the presence of even trace amounts of water, making it unsuitable for any practical applications.[1]

See also[edit]

References[edit]

  1. ^ Vedachalam, Murugappa; Ramakrishnan, Vayalakkavoor T.; Boyer, Joseph H.; Dagley, Ian J.; Nelson, Keith A.; Adolph, Horst G.; Gilardi, Richard; George, Clifford; Flippen-Anderson, Judith L. (1991). "Facile synthesis and nitration of cis-syn-cis-2,6-dioxodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine". The Journal of Organic Chemistry. 56 (10): 3413–3419. doi:10.1021/jo00010a043.


source: https://en.wikipedia.org/w/index.php?title=HHTDD&diff=1094871332&oldid=830043129

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