Cl-14

[rdxhmx]

Does anybody ever heard of CL-14?

[IDTB]

You've obviously overlooked the rules.

You're a newbie, which states you should think long and hard before creating new threads. Not only did you create a new thread, but you created a new thread with a one liner that gives us almost jackshit to work with. I've done a google search for "CL-14" which came up with 23,500 results. Look through them.

Oh, proper english grammer is highly appreciated. "HAS anybody" etc. etc.

[nbk2000]

Ever hear of searching?

Death.

[megalomania]

While the question certainly lacks the minimum standard acceptable for the board, a search of The Forum reveals no other sources of information for CL-14. As I have recently acquired some info on it myself, I shall share what I know for the benefit of others.

CL-14 is an acronym for your pick of the following names: 5,7-dinitro-2,1,3-benzoxadiazole-4,6-diamine 3-oxide; 5,7-dinitro-4,6-benzofurazandiamine 3-oxide; 4,6-dinitro-5,7-diaminobenzofuroxan; or 5,7-diamino-4,6-dinitrobenzofuroxan. The molecular formula is C₆H₄N₆O₆ and the CAS number is 117907-74-1. CL-14 is a designation given to it by the inventors at I believe Sandia National Laboratories. There is one reference I know of for its preparation, “Chemistry of (5-cyanotetrazolato-N2)pentaamminecobalt(III) perchlorate and similar explosive coordination compounds” by Lieberman, Morton L of Sandia National Laboratories in the Journal Industrial & Engineering Chemistry Product Research and Development (1985), 24(3), 436-40.

There is surprisingly little other information of value in the available literature. I believe there are a few documents on the Internet that reference it, but nothing useful that I have seen.

This explosive was first reported by Norris in the late 80’s in a journal I will probably never be able to get, but is none the less worth reporting: “CL-14, a High Performance Insensitive Explosive”, NWC TP 6955, Naval Weapons Center, China Lake, CA. If anybody knows how to get reports from the naval weapons Center I would LOVE to know :)

Ahh, yes, I almost forgot the piece de resistance US patent 4,754,040 “A method of preparing 4,6-dinitro-5,7-diaminobenzofuroxan from 4,6-dichloenzofuroxan.” This patent gives the synthesis of CL-14. Now then, the beginning of this process starts with 2-nitroaniline, and 4 steps later you get the precursor mentioned in the patent, 4,6-dinitro-5,7-dichlorobenzofuroxan. Unfortunately I do not yet know what those 4 steps are…

Oh, there is another published route: Synthesis of 5,7-diamino-4,6-dinitrobenzofuroxan” from Int. Ann. Conf, ICT, 21st (The 21st international annual conference of the ICT) paper 58. The paper is by Boren and Zhiyuan. This method developed by the Chinese starts from 2,4,6-trihalo-1,3-dinitrobenzene (where the halogen can be either chlorine or bromine)- it is reacted with NaN₃ in DMF, then with 100% nitric acid. Finally it is refluxed in toluene with some acetic acid and viola CL-14. The yields are reported to be somewhat lower by this method.

There are a slew of furoxan ring containing substances being developed out there nowadays. Why is it, though, that the best work is being done by the Chinese? Oh I don’t care that they do the research, they just don’t report any of their findings in ENGLISH! It is dreadful to find journal after journal and a host of patents written all in Chinese :( I don’t speak Chinese, I don’t know anyone who does, and translating their documents would cost me money. Maybe Acrobat 2020 will have universal bablefish eh?

EDIT: I'm sorry, I have made a big error! I looked at the wrong reference for CL-14, the journal reference “Chemistry of (5-cyanotetrazolato-N2)pentaamminecobalt(III) perchlorate and similar explosive coordination compounds" is incorrect. It should be:
Synthesis, characterization and explosive properties of benzofuroxans. Mehilal, A. K. Sikder; Sikder, Nirmala. High Energy Materials Research Laboratory, Pune, India. Indian Journal of Heterocyclic Chemistry (2001), 11(2), 149-154

Substituent effects in the conversion of azido- and diazidotrinitrobenzenes to benzofuroxans and difuroxans. Chaykovsky, Michael; Adolph, Horst G. Energ. Mater. Div., Nav. Surf. Warf. Cent., Dahlgren, VA, USA. Journal of Heterocyclic Chemistry (1991), 28(6), 1491-5

Synthesis of 5,7-diamino-4,6-dinitrobenzofuroxan. Chen, Boren; Liao, Zhiyuan. Dep. Chem. Eng., Beijing Inst. Technol., Beijing, Peop. Rep. China. International Annual Conference of ICT (1990), 21st(Technol. Polym. Compd. Energ. Mater.), 58/1-58/4

There is also US patent application 1990-519625, and US patent 5,039,812. I was looking at the references for the explosive CP, not CL-14. All the other references I mentened are correct.

[cutefix]

Ahh, yes, I almost forgot the piece de resistance US patent 4,754,040 “A method of preparing 4,6-dinitro-5,7-diaminobenzofuroxan from 4,6-dichloenzofuroxan.” This patent gives the synthesis of CL-14. Now then, the beginning of this process starts with 2-nitroaniline, and 4 steps later you get the precursor mentioned in the patent, 4,6-dinitro-5,7-dichlorobenzofuroxan. Unfortunately I do not yet know what those 4 steps are…
It was stated in the US Patent # 5,136,041
1)Where the 3-nitro aniline(meta nitroaniline?) is converted to tetranitroaniline in the same manner that picric acid is prepared by reacting first with sulfuric acid and then followed by nitration with nitric acid .
2)Then the conversion of the tetranitroaniline through 3-azido-2,4,6-trinitroaniline by reaction with NaN3.
3)where the intermediate is allowed to decompose to obtain the
7-Amino-4,6-dinitrobenzofuroxan (ADNBF.
4) Finally the ADNBF is converted to CL-14 by alkaline reaction with hydroxylamine hydrochloride in KOH as shown in US Patent# H1,078
The resulting potassium salt is reacted with HCl to yield the pure CL-14.
This looks interesting for explosive hobbyists but you have to find a practical source for 3 -nitro aniline;or it can be synthesized from a French site:
http://www.google.com.au/search?q=cache:eT4lTP6Zo8UJ:www.educnet.education. fr/rnchimie/bts_c/annales/tp/1997/6_session_1997_c.pdf+3-+nitroaniline&hl=en&ie=UTF-8
And mega you have your own synthesis also:
http://roguesci.org/megalomania/synth/synthesis3.html
hydroxylamine HCL is available commercially:
http://www.klausfmeyer.de/hcl.htm
But it can also be synthesized from this site:
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0318
and the use the sodium azide from the car airbags why not
Therefore the practicality of home synthesis is there.
How about that mega?

;)

[nitriees]

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There are a slew of furoxan ring containing substances being developed out there nowadays. Why is it, though, that the best work is being done by the Chinese? Oh I don’t care that they do the research, they just don’t report any of their findings in ENGLISH! It is dreadful to find journal after journal and a host of patents written all in Chinese I don’t speak Chinese, I don’t know anyone who does, and translating their documents would cost me money. Maybe Acrobat 2020 will have universal bablefish eh?
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I have a friend good in chinese and with some chemical knowledge, can you send me the document and I will try to get it translate.

[Anthony]

Micotek has sucessfully synthesised 3-nitroaniline, detaails can be found in this thread:

http://www.roguesci.org/theforum/showthread.php?s=&threadid=3158