Sciencemadness Discussion Board

1,2,3-triazidopropane

PHILOU Zrealone - 13-7-2011 at 06:53

Does someone here have some info on 1,2,3-triazidopropane?
Like density, mp, bp, heat of formation, critical temperature of explosion, VOD, etc

I already have infos on azido methane, and 1,2-diazidoethane and I would like to go one step further.

I know it exists because it is used to produce triaminopropane via reduction. It is said to be very explosive.

It is probably done via 1,2,3-trichloropropane (or tribromo brother) and NaN3 similar to the two others.

More likely very toxic like the two others because azido and nitrile groups displays the halogen like behavior and are thus succeptible of hydrolysis to produce HCN or HN3...

On a side note I have read today about diazoturomethane (methylendiazide-diazidomethane(*) CH2(N3)2) and triazoturomethane (azidoform-triazidomethane CH(N3)3) as being very sensitive compounds made by reaction of methylene chloride or chloroform on NaN3 in a suitable solvent.
Both are hell sensitive explosive!
(*) Not to be confused with diazomethane CH2N2

[Edited on 13-7-2011 by PHILOU Zrealone]

quicksilver - 13-7-2011 at 14:45

This is as close as I got. There MAY be some better material in the notes and sited material within.
Independent specifics on triazidopropane wasn't in the common sources. But Wiley-InterScience may have some newer research material


edit:
I had to reduce the file size (it went over 2Mb) It has graphics but they came out fair when reduced. It's most likely not exactly what you want (specifics) but it may have some material allegorical to your interest in the material.

Attachment: Klapotke.pdf (694kB)
This file has been downloaded 742 times



[Edited on 13-7-2011 by quicksilver]

franklyn - 13-7-2011 at 18:12

Quote: Originally posted by PHILOU Zrealone  
Does someone here have some info on 1,2,3-triazidopropane?
Like density, mp, bp, heat of formation, critical temperature of explosion, VOD, etc.
I know it exists because it is used to produce triaminopropane via reduction.
It is said to be very explosive.


Indeed, then how could one observe those properties in such a material ?
Realize that this is the azide analog of glyceryl trinitrate.
This examines similar compounds ( but not 1,2,3-triazidopropane )

Energetic Azido Compounds ( specifically azido alkanes )
www.dtic.mil/dtic/tr/fulltext/u2/a083770.pdf

.

PHILOU Zrealone - 13-7-2011 at 23:59

Thanks Quicksilver,
I have found that document just one hour prior to my posting here...quite interesting because it lists 1,2,3-trinitramino-propane what was also one of my molecule of interest.

I'm also interested in 1,2,3-triaminopropane but I only find references to HCl salts of it, not the free-base pure substance.

Thanks Franklyn,
I don't think it is as critical as it may look because although powerfull similar molecules of that azido alcane familly are of "moderade" sensitivity (about the sensitivity of nitrate esters):
Methyl azide and 1,2-diazidoethane are sensitive to shock, to friction and to heat.

True that 1,2,3-triazidopropane might be a solid what may be a problem regarding sensitivity to friction

I think that I will have to make a minute amount trial to find out physico-chemical properties (density and other parameters)



[Edited on 14-7-2011 by PHILOU Zrealone]

quicksilver - 14-7-2011 at 12:27

I thought you'd get it prior to me.
When you come up with a tough one; you find a tough one! Just out of curiosity I looked around.....I couldn't find ANYTHING other than a mere mention of the chemical.
I will try the monographs when I get a chance to use the subscription and of course I'll post what I find......if anything... :-(

497 - 14-7-2011 at 14:01

Dichlorocarbene + olefin of your choice --> gem-diclorocyclopropane
Could diazidocyclopropane or substituted versions be potentially useful?
Maybe 1,1-diazido-2-trinitrophenyl cyclopropane?

How hard is it to make tribromocylclopropane?

AndersHoveland - 17-7-2011 at 15:03

If I remember correctly, tetrazidomethane C(N3)4 had a surprisingly low detonation velocity considering all the nitrogen atoms, I think it was somewhere between 4 to 6.5 km/sec, but now I cannot find any sources.
The reason for this is probably that the nitrogen-carbon bonds are unusually strong because of the electron-withdrawing effect of the azido groups. My opinion is that azido groups add much sensitivity, and only incremental gains in power to explosive molecules. They are not really worth it. Much better to incorporate tetrazole or 1,2,3-triazole rings, which are much more stable.