Take the 2-minute tour ×
Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers and students. It's 100% free, no registration required.

A lot of the organometallics are rather... interesting compounds to work with. The most famous (among those who care, anyway) is tert-butyllithium or t-BuLi. It is the textbook example of a pyrophoric substance, demonstrated to pretty much every chemistry major as an air-sensitive chemical requiring special handling (Syringe and cannula transfers, gas-tight septa, argon/nitrogen blankets, that kind of thing). Despite the inherent hazards of the stuff, it's widely used in the industry (hence widespread notoriety) to add butyl groups to an organic molecule (most organometallics are useful for this kind of carbon-carbon bond formation), and you can buy it by the - airtight - gallon canister.

There are, surprisingly (except to most organic chemists), even more dangerous compounds in the average organic chemistry lab. Along the pyrophoric line, many of the multi-methyl-metallics are violently pyrophoric (even compared to BuLi), including trimethylaluminum, dimethylzinc, and dimethylmagnesium. All of these are also extremely poisonous (anything these compounds can do to your wonder-drug-in-progress, they can also do to various key structures in your own body), with dubious honors reserved for dimethylmercury. Because many of these, especially the organoalkaline compounds, react violently with water, they also automatically rate at least a 3 on the "reactivity" scale.

When leads me to wonder, because I wonder about these things from the safety of my office chair in a completely unrelated field; just how bad can it get? Specifically, is there any compound with an accepted use in laboratory or industrial application that is nasty enough to max out the entire NFPA-704 diamond? The closest I can find is trimethylaluminum, at a 3-4-3 (heath-fire-reactivity). T-BuLi is a 3-3-4. I can't find NFPA data on straight diazomethane (which may be because nobody in their right mind ever works with the stuff in its pure gaseous form; it's always used in a dilute diethyl ether solution, and even then is never sold or shipped that way) but it would probably be a finalist, as the gas is acutely toxic, autoignites at room temperature, and detonates on standing (something for everyone!). I'm thinking that these two inorganic families - light alkyl-metallics and organo-polyazides - would be the most likely candidates to produce a compound so toxic, so flammable, and so readily reactive, yet so interesting to chemistry, that the NFPA would see fit to rate it, and would give it highest honors.

share|improve this question
    
There's t-BuOOH but one source (cited by the Wikipedia stub article) says it's 4-4-4 while another source says it's 1-4-4... –  BoltClock Feb 12 '13 at 8:26
    
@BoltClock and other sources have it at different values… it depends how it is conditioned (in solvent, or adsorbed on porous substrates, …). As the question say, noöne in their right mind would sell it in a form where it is 4-4-4 (and noöne would probably buy it, because it would hardly be usable!) –  F'x Feb 12 '13 at 8:37
    
Diborane is a pleasant 4-4-3. Seriously, that stuff is nuts. Nice example of 3c2e bonding though. Hydrazine is also 4-4-3. –  Richard Terrett Feb 12 '13 at 10:36
    
I found a MSDS for diazomethane but it is not a very good one. However, all signs point to 4-4-4. –  Ben Norris Feb 12 '13 at 11:39
    
Tert-butylhydroperoxide looks promising. One nitpick (which doesn't disqualify it as I didn't require it) is that it doesn't react strongly to water (it gets its 4 for reactivity from its strong oxidation qualities and its propensity as a peroxide to explode spontaneously). You still can't use water to fight this fire, but you can use foam. –  KeithS Feb 12 '13 at 18:24
show 2 more comments

3 Answers 3

up vote 7 down vote accepted

Answering my own question based on the comments, tert-butyl-hydroperoxide is at least one such chemical. As stated on this MSDS from a government website, it's a 4-4-4, with additional special warning of being a strong oxidizer. The only thing that it does not do that could make the 704 diamond any worse is react strongly with water. It is in fact water soluble, though marginally, preferring to float on top (and therefore traditional water-based fire suppression is ineffective, but foam/CO2 will work).

I will refrain from giving my own answer the checkmark for now; if anyone else can find a chemical that, in a form that is used in the lab or industrially, is a 4-4-4 that is a strong oxidizer and reacts strongly with water, that's pretty much "as bad as it gets".

share|improve this answer
add comment

Ethyl nitrite is rated 4-4-4 but it does not have anything on the white square. Pentaborane has a good 4-4-4-W. However it's not an oxidizer.

share|improve this answer
add comment

monomethyl hydrazine................

share|improve this answer
1  
Can you expand on the answer a bit, this doesn't explain why,for example. –  jonsca Nov 30 '13 at 8:10
1  
Why did this get downvotes? Sure it is an extremely short answer, but it is still valid (as you can check here: en.wikipedia.org/wiki/Monomethylhydrazine). The question is whether there is any substance with 4-4-4. This answer provides an example. I agree with @jonsca that it could be expanded a bit to save readers the effort of looking it up themselves, but still... –  Michiel Nov 30 '13 at 11:55
2  
@Michiel Good answers on this and other stack exchange sites always give enough context for users not to have to check the answer externally. If you want up votes include some context and examples to show why mono methyl hydrazine is a good answer. –  matt_black Jan 2 at 13:13
add comment

Your Answer

 
discard

By posting your answer, you agree to the privacy policy and terms of service.

Not the answer you're looking for? Browse other questions tagged or ask your own question.