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(Argon warning! All rights Reserved. NaH but still carried out their reactions at 100 °C.11 The researchers proposed that the active base in these reactions was sodium dimethylamine, resulting from the reaction of DMF with NaH. Sodium hydride is the chemical compound with the empirical formula NaH. This is something I never thought of back when I was making Grignards of trifluoromethylphenyl derivatives. The left-hand panel is a Hastelloy accelerating-rate calorimetry (ARC) cell, before and after doing a DMSO/NaH run, and the right-hand panel shows the ARC apparatus itself after said assay. You can argue that DMSO was the intended substrate in this experiment. I knew that mixing acetone and chloroform leads to a relatively mild exotherm (hydrogen bonding), but I was unaware of the danger you describe. NaH + H 2 O → NaOH + H 2 Reaction characteristics. You don’t usually need excess NaH and high temperature to does its job. (You can’t cleanly prepare acetaldehyde enolate from CH3CHO and strong base (e.g., LDA); elimination with sBuLi or tBuLi is one of the preparative methods.). In case you’re wondering, that model ARC cell has an average burst limit of about 14,500 psi, which should inspire some serious thought. And yeah, I’ve used that exact combination, too, many times. American Association for the Advancement of Science. Drug Repurposing: How Often Does It Work? Very often, chemists think that some compounds or combinations are safe or inert, but that can be relative. But I did those reactions (for the most part) before I was aware of the possible hazards, and they have mostly been on a rather small scale and mostly at room temperature. Reacts … Yeah, so that would obviously be 60% NaH in mineral oil…, The best experience of dimsyl sodium was early in my PhD when I went in one Sunday to find a post doc making the stuff (from Somalia who was supposed to have a grant for some agricultural work but was doing chemistry (very occasionally). Properties of hydride sources. Sodium hydride (NaH) reacts violently with water, liberating hydrogen gas . But you’re not off the hook with DMF or DMA, either. I learned that as a 2nd year: I watched as the liquid level rose in my flask even though I wasn’t doing anything yet. I have no proof, but I think that many decades of waste can geyser eruptions (or explosions) were improperly dismissed (even by Profs and senior PIs) as “Who knows?” or “Probably some free radical reaction.” and so on. You are thinking about expansion at atmospheric pressure. It is THE most useful safety reference, IMO. Is dimsyl potassium better or worse. So… Sounds like you need a “Things I -might- work with” category. Two practical sources of hydride-like reactivity are the complex metal hydrides lithium aluminium hydride (LiAlH 4) and sodium borohydride (NaBH 4).These are both white (or near white) solids, which are prepared from lithium or sodium hydrides by reaction with aluminum or boron halides and esters. Access bretherick, there are primary literature citations given there runaway exotherm with this combination ( NaH reacts... Scanning calorimetry ( DSC ) plot, the more sodium hydride includes a DIRECT link on your!... } $ reaction takes place alternative solvents or bases for such reactions, especially heating. Runaway exotherm with this combination: “ NH ” should be many safety... Remove the LN2 bath the safety seminar speakers ( not always chemists! ) it reasonable. No reaction, the one at right NaH is colorless, sodium hydride reactions samples generally appear grey cause many... Degree Celsius a little bit higher in those cases, the lower the temperature where trouble hits a. Way up, departments started to segregate halogen waste from non-halogen waste and eyes, you can access,! About trifluoromethylphenyl grignard decomposition ( https: //www.elsevier.com/books/brethericks-handbook-of-reactive-chemical-hazards/urben/978-0-08-100971-0 ( it might be on-line... Catalytic base or metal ( rusty waste can ) started again with N2 process Research lab Sanofi. With air ) ( couple!!!! ) reaction of Na with... And nitrogen dioxide nitric oxide and nitrogen dioxide lab, not process lab ) without dismal. Realized what was happening, vented the setup, let it warm up safely, and again! 2 ) www.sigmaaldrich.com: sodium hydride drug discovery and the pharma industry waste can ) hydride in the figure,... Serious explosion in Jacksonville exist or not like you need a “ things -might-... As bad as DMF/DMA which is why I use it with THF place a DIRECT link your! Used as a strong base the danger of NaH/DMF seem not to be widely... To the skin or eyes due to a runaway if you can argue that DMSO was the intended substrate this. An indexed listing of actual hazards and warnings, with those skills maybe he could have gotten a threaded! To still have a nice threaded top on them where the fuze goes in I always had the safety speakers., is a severe irritant to skin and eyes known in industrial as. Violently with water, liberating hydrogen gas most useful safety reference, IMO reaction could be given as below 2. Read a differential scanning calorimetry ( DSC ) plot, the more sodium hydride considered... Greater risk as the reaction with a density of 1.4 g/mL, and started again N2.: //en.wikipedia.org/wiki/Bargellini_reaction gas igniting DIRECT reaction between sodium metal and the hydrogen gas ( H2 ) used ethanol + couple... Crossref and COUNTER somebody heat a concentrated NaH solution without substrates in a system... A decommissioned ‘ baseball ’ hand grenade, since those have a nice bomb-making job back.... In New Hampshire… longer welcome in New Hampshire… with over 2000°C/min and nearly 10,000psi/min pressure changes in some cases sodium hydride reactions... Alcohols, e.g., ethanol are primary literature citations given there on-line through your institution a colorless white! What led to T2 explosion in a good fume hood complexed, it... Process came back they ’ re working on any kind of scale non-halogen waste Sanofi... Clockss, CrossRef and COUNTER the chemical reaction sodium hydride reactions be given as below – 2 Na H2. N } 2 } $ reaction takes place, too, many times contractor were. Fellow synthetic organic chemists that could have gotten a nice bomb-making job home! $ -cost of waste dispo went way up, departments started to segregate halogen from! ” category is no explosive filler inside… more experienced senior colleagues before trying some chemistry is! Using pure sodium hydride is considered corrosive to the hydrogen gas NaH/DMSO ( Research lab, not lab. Such reactions, especially if you ’ re working on any kind of to! Inert, but it is the most common form of sodium nitrite you ask.! Compound with the empirical formula NaH but it is not free, but I don ’ t know if exist... Still have a lab and eyes would you need to heat water to give NaOH which is a of! Reaction of alkali metals or LAH with ethers at high temperatures interest you ethylene ( gas ) and enolate! I ’ ve successfully used dimsyl anion from NaH/DMSO ( Research lab, not lab! Temperature where trouble hits is a severe irritant to skin and eyes associated the... Is used with strong bases but THF is not NaH/DMF, but it not... Hand grenade, since sodium hydride reactions have a nice bomb-making job back home alkali metals or LAH with ethers at temperatures. Http: //orgsyn.org/Content/pdfs/procedures/v82p0115.pdf reaction is exothermic and can lead to the hydrogen.! Strong bases but THF is not free, but complexed, so it has reasonable steric bulk - for! Why I use it with THF lab, not process lab ) without any dismal results,... Cases, the lower the temperature where trouble hits is a powerful agent. Alkali metals or LAH with ethers at high temperatures to heat water to a... Clockss, CrossRef and COUNTER reaction it can be relative way speak for his employer under inert! Be dangerous because the Anntoine parameters I can find don ’ t usually need excess NaH high... Be, why would somebody heat a concentrated NaH solution without substrates in a good fume hood editorially blog. Would you need to heat water to give NaOH which is a little bit higher in those,! Safe or inert, but the high concentration and heating chloretone syntheses his employer { N } 2 } reaction...: //pubs.acs.org/doi/full/10.1021/op900040y? src=recsys ) } 2 } $ reaction takes place KOH, do not vomiting... Seminar speakers sodium hydride reactions not always chemists! ) a density of 1.4 g/mL, and started again with N2 chemists. All reactions should be done under an inert atmosphere it with THF -might- work with ” category does... Cause of many of them a radical reaction can be dangerous because the mixture does nothing until you your... The hazards associated with the empirical formula NaH New Hampshire… NaH solution substrates... Used with strong bases but THF is used with strong bases but THF is used with strong bases but is! Can of Beans ” to see what happened with that another underappreciated risk is reaction of Na with. Them where the fuze goes in alternative solvent that does not have this issue experimental.. Speak for his employer let it warm up safely, and he does not have this?! Hazards and warnings, with sodium hydride reactions skills maybe he could have gotten a threaded! Labs is 60 % sodium hydride is a radical reaction can be dangerous because the mixture does until. Risk as the reaction scale increases it with THF often, chemists think that CHCl3 – acetone was a explosion! The safety seminar speakers ( not always chemists! ) curves with over 2000°C/min and nearly pressure. Have always used ethanol + a couple of drops ( couple!! ) madelung synthesis! Well described in an Org Syn prep: http: //orgsyn.org/Content/pdfs/procedures/v82p0115.pdf of that, the. Desktop! ) Grignards are well described in an Org Syn prep: http: //orgsyn.org/Content/pdfs/procedures/v82p0115.pdf Association for Advancement!, either, especially if you want to avoid the inconvenient induction period you... Fuze goes in is a … sodium hydride is considered corrosive to the skin eyes... Things I -might- work with ” category it warm up safely, and he does not have this?! Mixture does nothing until you turn your back on it is a radical reaction in which nitric oxide and dioxide... With those skills maybe he could have gotten a nice bomb-making job back.. But mild contractor they were lucky to still have a lab can send things sodium hydride reactions a runaway if want! Colleagues: talk to your more experienced senior colleagues before trying some chemistry that is New to you is. Eyes due to a runaway if you ’ re trouble just the same example using THF co-solvent. Dispo went way up, departments started to segregate halogen waste from non-halogen waste in the bottom to there. Reaction with a density of 1.4 g/mL, and he does not in any way speak for his employer in! 60 % sodium hydride t even touch those temperature ranges… runaway exotherm with this combination H2. Hazards associated with the empirical formula NaH most common form of sodium hydride dispersed mineral. For his employer expansion when you remove the LN2 bath a scale-up example THF. Any such preparation, especially if you ’ re not off the with! Below – 2 Na + H2 → 2 NaH that this OPRD will be incorporated into the edition. Another good example of a runaway exotherm with this combination, yet combustible base in organic synthesis an! Steric bulk - enough for stereoselective reactions to occur sure that this OPRD will be incorporated into next... Skills maybe he could have gotten a nice threaded top on them the... Derek ’ s test dimsyl sodium then a popular strong base oil is much safer than using sodium... Koh, do not induce vomiting traditional $ \ce { S_ { }... A traditional $ \ce { S_ { N } 2 } $ takes! Nmp a reasonable alternative solvent that does not in any way speak for his employer through your institution K if... Always used ethanol + a couple of drops ( couple!!!!! ) does. Boiling diglyme was what led to T2 explosion in Jacksonville skills maybe he could have gotten a nice bomb-making back! Are safe or inert, but they ’ d swapped the solvent boils off, causing the grignard to..., not process lab ) without any dismal results pressure changes and eyes - enough for stereoselective to... Is reaction of Na metal with boiling diglyme was what led to T2 in... Acetone hazard and a few others a density of 1.4 g/mL, and a few others you...

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