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Revision as of 20:19, 21 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|error← Previous edit		Latest revision as of 17:43, 31 December 2024 edit undoTrasheater Midir (talk | contribs)Extended confirmed users3,587 editsm Paragraph edited #MiniEdit
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	{{Chembox		{{Chembox
			| Verifiedfields = changed
	| verifiedrevid = 445677431
			| Watchedfields = changed
			| verifiedrevid = 451734664
	| ImageFileL1 = CL-20.svg		| ImageFileL1 = CL-20.svg
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		| ImageFileL1_Ref = {{chemboximage|correct|??}}
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	| ImageFileR1_Ref = {{chemboximage|correct|??}}		| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ImageSizeR1 = 121		| ImageSizeR1 = 121
	| ImageNameR1 = Ball and stick model of hexanitrohexaazaisowurtzitane		| ImageNameR1 = Ball and stick model of hexazaisowurtzitane
	| IUPACName = 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane{{Citation needed|date = May 2011}}		| IUPACName = 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclododecane
	| OtherNames = CL-20		| OtherNames = {{Unbulleted list
			| CL-20
	| Section1 = {{Chembox Identifiers
			| Hexanitrohexaazaisowurtzitane
	| Abbreviations = CL-20, HNIW
			| 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane
	| CASNo = 135285-90-4
			| Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazopyrazine
	| PubChem = 9889323
			| HNIW
	| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
			}}
	| PubChem1 = 11048432
			|Section1={{Chembox Identifiers
	| PubChem1_Ref = {{Pubchemcite|correct|pubchem}}
			| Abbreviations = CL-20, HNIW
	| PubChem1_Comment = <small>(3''R'',9''R'')-dodec</small>
			| CASNo_Ref = {{cascite|correct|??}}
	| PubChem2 = 11419235
			| CASNo = 135285-90-4
	| PubChem2_Ref = {{Pubchemcite|correct|pubchem}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem2_Comment = <small>(3''R'',5''S'',9''R'',11''S'')- dodec</small>
			| UNII = RQM82X0CL7
	| ChemSpiderID = 8064994
			| PubChem = 9889323
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| PubChem1 = 11048432
	| ChemSpiderID1 = 9223599
			| PubChem1_Comment = <small>(3''R'',9''R'')-dodec</small>
	| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
			| PubChem2 = 11419235
	| ChemSpiderID1_Comment = <small>(3''R'',9''R'')-dodec</small>
			| PubChem2_Comment = <small>(3''R'',5''S'',9''R'',11''S'')- dodec</small>
	| ChemSpiderID2 = 9594121
			| ChemSpiderID = 8064994
	| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID2_Comment = <small>(3''R'',5''S'',9''R'',11''S'')- dodec</small>
			| ChemSpiderID1 = 9223599
	| SMILES = o:n(:o)N1C2C3N(C4C(N3n(:o):o)N(C(C1N4n(:o):o)N2n(:o):o)n(:o):o)n(:o):o
			| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
	| SMILES1 = (=O)N1C2C3N(C4C(N3()=O)N(C(C1N4()=O)N2()=O)()=O)()=O
			| ChemSpiderID1_Comment = <small>(3''R'',9''R'')-dodec</small>
	| StdInChI = 1S/C6H6N12O12/c19-13(20)7-1-2-8(14(21)22)5(7)6-9(15(23)24)3(11(1)17(27)28)4(10(6)16(25)26)12(2)18(29)30/h1-6H
			| ChemSpiderID2 = 9594121
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
	| StdInChIKey = NDYLCHGXSQOGMS-UHFFFAOYSA-N
			| ChemSpiderID2_Comment = <small>(3''R'',5''S'',9''R'',11''S'')- dodec</small>
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 77327
			| SMILES = (=O)N1C2C3N(C4C(N3()=O)N(C(C1N4()=O)N2()=O)()=O)()=O
			| StdInChI = 1S/C6H6N12O12/c19-13(20)7-1-2-8(14(21)22)5(7)6-9(15(23)24)3(11(1)17(27)28)4(10(6)16(25)26)12(2)18(29)30/h1-6H
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChIKey = NDYLCHGXSQOGMS-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = {{Chem|C|6|N|12|H|6|O|12}}		| Formula = {{Chem|C|6|N|12|H|6|O|12}}
	| MolarMass = 438.1850 g mol<sup>-1</sup>		| MolarMass = 438.1850 g mol<sup>−1</sup>
	| ExactMass = 438.022813716 g mol<sup>-1</sup>		| Density = 2.044 g cm<sup>−3</sup>
	}}
	| Section6 = {{Chembox Explosive
	| ExplosiveV = 9.38 km s<sup>-1</sup>
	}}		}}
			|Section6={{Chembox Explosive
			| DetonationV = 9,500 ]
			| REFactor = 1.9 }}
	}}		}}
	'''2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane''', also called '''HNIW''', and '''CL-20''', is a ] explosive with the formula C<sub>6</sub>H<sub>6</sub>N<sub>12</sub>O<sub>12</sub>, developed by the ] facility, primarily to be used in ]s. It has a better ]-to-] ratio than conventional ] or ]. It produces 20% more energy than traditional HMX-based propellants, and is widely superior to conventional high-energy propellants and explosives.		'''Hexanitrohexaazaisowurtzitane''', also called '''HNIW''' and '''CL-20''', is a ] ] explosive with the formula {{chem2|C6H6N12O12}}. It has a better ]-to-] ratio than conventional ] or ]. It releases 20% more energy than traditional HMX-based propellants.
			== History and use ==
	While most development of CL-20 has been fielded by the ], the ] (through ]) has also been interested in CL-20 for use in ]s, such as for ], as it has lower observability characteristics (e.g., less visible smoke).<ref></ref>
			In the 1980s, CL-20 was developed by the ] facility, primarily to be used in ]s.<ref>{{cite web | last=Kadam | first=Tanmay | title=Pioneered By The US, China 'Racing Ahead' Of Its Arch Rival In 'CL-20' Tech That Propels PLA's Deadly Missiles | website=Eurasian Times | date=2023-03-11 | url=https://eurasiantimes.com/pioneered-by-the-us-china-races-ahead-of-its-arch-rival/}}</ref>
			While most development of CL-20 has been fielded by the ], the ] (through ]) has also been interested in CL-20 for use in ]s, such as for ], as it has lower observability characteristics such as less visible smoke.<ref>{{cite web |url=http://www.physorg.com/news/2011-09-university-chemists-stabilize-explosive-cl-.html |title=University chemists devise means to stabilize explosive CL-20 |first=Bob |last=Yirka |publisher=Physorg.com |date=9 September 2011 |accessdate=8 July 2012 |archive-date=25 January 2021 |archive-url=https://web.archive.org/web/20210125151129/https://phys.org/news/2011-09-university-chemists-stabilize-explosive-cl-.html |url-status=live }}</ref>
	CL-20 has not yet been fielded in any production weapons system, but is presently undergoing testing for stability, production capabilities, and other weapons characteristics.
			Thus far, CL-20 has only been used in the ] 300 “kamikaze” drone, but is undergoing testing for use in the Lockheed Martin ]C Long Range Anti-Ship Missile (LRASM) and AGM-158B Joint Air-to-Surface Standoff Missile-Extended Range (JASSM-ER).<ref>{{Cite web |last=Wolfe |first=Frank |date=2023-03-28 |title=CL-20 Used in Switchblade 300, May See Wider Use in JASSM-ER, LRASM, Other Munitions |url=https://www.defensedaily.com/cl-20-used-in-switchblade-300-may-see-wider-use-in-jassm-er-lrasm-other-munitions/advanced-transformational-technology/ |access-date=2024-04-26 |website=Defense Daily |language=en-US}}</ref>
	==Synthesis==
	It is made from ], ], ], and white fuming ] by combining these chemicals.
			The ] have also looked into CL-20.<ref>{{cite web | url=https://pib.gov.in/newsite/PrintRelease.aspx?relid=67872 | title=Pune Based DRDO Lab Makes Most Powerful Conventional Explosive }}</ref>
	]
			The Taiwanese ] innaugerated a CL-20 production facility in 2022 with reported integration into the ] and ] product lines.<ref>{{cite web |last1=Tien-pin |first1=Lo |last2=Chung |first2=Jake |title=Institute develops powerful explosive |url=https://www.taipeitimes.com/News/front/archives/2024/07/06/2003820398 |website=taipeitimes.com |date=6 July 2024 |publisher=Taipei Times |access-date=7 July 2024}}</ref>
			== Synthesis ==
			]
			First, ] ('''1''') is condensed with ] ('''2''') under acidic and dehydrating conditions to yield the first intermediate compound.('''3'''). Four benzyl groups selectively undergo ] using ] and hydrogen. The amino groups are then acetylated during the same step using ] as the solvent. ('''4'''). Finally, compound '''4''' is reacted with ] and ], resulting in HNIW.<ref>{{cite journal|journal = ]|year = 2005|volume = 41|issue = 2|pages = 121–132|title = Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations (review)|first1 = U. R.|last1 = Nair|first2 = R.|last2 = Sivabalan|first3 = G. M.|last3 = Gore|first4 = M.|last4 = Geetha|first5 = S. N.|last5 = Asthana|first6 = H.|last6 = Singh|doi = 10.1007/s10573-005-0014-2|s2cid = 95545484}}</ref>
			==Cocrystals==
			In August 2011, ] and ] published results showing that a ] of CL-20 and ] had twice the stability of CL-20—safe enough to transport, but when heated to {{convert|136|°C|°F}} the cocrystal may separate into liquid TNT and a crystal form of CL-20 with structural defects that is somewhat less stable than CL-20.<ref>{{cite journal|doi=10.1002/anie.201104164 | pmid=21901797 | volume=50 | issue=38 | title=Improved Stability and Smart-Material Functionality Realized in an Energetic Cocrystal | year=2011 | journal=Angewandte Chemie International Edition | pages=8960–8963 | last1 = Bolton | first1 = Onas| hdl=2027.42/86799 | hdl-access=free }}</ref><ref>{{Cite web |url=https://www.science.org/content/blog-post/things-i-won-t-work-hexanitrohexaazaisowurtzitane |title=Things I Won't Work With: Hexanitrohexaazaisowurtzitane |date=11 November 2011 |access-date=2016-01-04 |archive-date=2015-09-03 |archive-url=https://web.archive.org/web/20150903002615/http://blogs.sciencemag.org/pipeline/archives/2011/11/11/things_i_wont_work_with_hexanitrohexaazaisowurtzitane |url-status=live }}</ref>
			In August 2012, ] et al. published results showing that a ] of 2 parts CL-20 and 1 part ] had similar safety properties to HMX, but with a greater firing power closer to CL-20.<ref>{{cite journal|doi=10.1021/cg3010882 | volume=12 | issue=9 | title=High Power Explosive with Good Sensitivity: A 2:1 Cocrystal of CL-20:HMX | year=2012 | journal= Crystal Growth & Design| pages=4311–4314 | last1 = Bolton | first1 = Onas}}</ref><ref>{{cite web | title=Powerful new explosive could replace today's state-of-the-art military explosive | website=spacewar.com | date=2012-09-06 | url=http://www.spacewar.com/reports/Powerful_new_explosive_could_replace_todays_state_of_the_art_military_explosive_999.html | archive-url=https://web.archive.org/web/20120909160217/http://www.spacewar.com/reports/Powerful_new_explosive_could_replace_todays_state_of_the_art_military_explosive_999.html | archive-date=2012-09-09 | url-status=live}}</ref>
			==Polymeric derivatives==
			In 2017, K.P. Katin and M.M. Maslov designed one-dimensional covalent chains based on the CL-20 molecules.<ref name=katin2017>{{cite journal|doi=10.1016/j.jpcs.2017.04.020 | volume=108 | title=Toward CL-20 crystalline covalent solids: On the dependence of energy and electronic properties on the effective size of CL-20 chains | year=2017 | journal=] | pages=82–87 | last1 = Katin | first1 = Konstantin P. | last2 = Maslov | first2 = Mikhail M.| arxiv=1611.08623 | bibcode=2017JPCS..108...82K | s2cid=100118824 }}</ref> Such chains were constructed using {{chem|CH|2}} molecular bridges for the covalent bonding between the isolated CL-20 fragments. It was theoretically predicted that their stability increased with efficient length growth. A year later, M.A. Gimaldinova and colleagues demonstrated the versatility of {{chem|CH|2}} molecular bridges.<ref name=gimaldinova2018>{{cite journal | doi=10.1039/c8ce00763b | volume=20 | issue=30 | title=Electronic and reactivity characteristics of CL-20 covalent chains and networks: a density functional theory study | year=2018 | journal=] | pages=4336–4344 | last1 = Gimaldinova | first1 = Margarita A. | last2 = Maslov | first2 = Mikhail M. | last3 = Katin | first3 = Konstantin P. }}</ref> It is shown that the use of {{chem|CH|2}} bridges is the universal technique to connect both CL-20 fragments in the chain and the chains together to make a network (linear or zigzag). It is confirmed that the increase of the effective sizes and dimensionality of the CL-20 covalent systems leads to their thermodynamic stability growth. Therefore, the formation of CL-20 crystalline covalent solids seems to be energetically favorable, and CL-20 molecules are capable of forming not only molecular crystals but bulk covalent structures as well. Numerical calculations of CL-20 chains and networks' electronic characteristics revealed that they were wide-bandgap semiconductors.<ref name="katin2017" /><ref name="gimaldinova2018" />
	==See also==		==See also==
			{{div col begin}}
	*]
			* ]
	*] (DDF)
			* ] (DDF)
	*]
			* ] (HNB)
	*]
			* ] (HNC)
	*]
			* ]
			* ] (N8)
			* ] (Wurtzitane)
			* ] (ONC)
			* ]
			* ]
			{{div col end}}
	==References==		== References ==
	{{Reflist}}
			{{reflist}}
			== Further reading ==
			* {{cite journal |title=Improved Stability and Smart-Material Functionality Realized in an Energetic Cocrystal |last=Bolton |first=Onas |author2=Adam J. Matzger |journal=] |volume=123 |issue=38 |pages=9122–9125 |date=September 12, 2011 |doi=10.1002/ange.201104164|pmid=21901797 |bibcode=2011AngCh.123.9122B |hdl=2027.42/86799 |hdl-access=free }}
			* Lowe, Derek (11 November 2011)
	]
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