Yup, and just as well I've been brushing up on my inert atmosphere technique. LiAlH4 has teeth, and it isn't shy about using them. Incredibly water-sensitive, air sensitive and generally with a bad attitude. Bursts into flame, and gives off massive clouds of instantly-evolved explosive hydrogen gas on contact with solvent that hasn't been super-thoroughly dried.
Usually used in either THF (tetrahydrofuran) or occasionally in diethyl ether, although I'll be using THF for my reductions with it, as THF is superior for the job with LAH, forms a complex which helps solubilize the LAH. Needs the solvent to be pre-dried with conventional dessicants, in a flask dried immediately before use with flame, or in an oven, and distilled after pre-drying from sodium metal pieces, after boiling it over the sodium, distilled under a current of dry nitrogen, argon or helium and used with a protective inert gas flow, without any trace of moisture of air present, otherwise it bursts into flame. Not pretty in a flammable solvent such as a liter of refluxing THF or ether.
Might even treat myself to some Red-Al, if I an afford it, Sodium bis(2-methoxyethoxy)aluminium hydride, it'd a lot more expensive than LAH, and one needs quite a lot of equivalents per mol. of substrate to be reduced, given its high molar mass compared to LiAlH4 (LAH, or Lith-Al for short), but its available as solutions in toluene, can reduce anything that LAH does AFAIK, and unlike LAH it isn't pyrophoric. I've never worked with Red-Al before, but it really does sound a pleasure to work with, like sodium borohydride is. NaBH4 won't reduce nitro groups to amines though sadly, which is one of the great things about LAH, but its so tame, it can even be used in aqueous solution in some reactions. Got a big bottle of borohydride, though, and haven't regretted it. Nice, stable, calm stuff, not pyrophoric at all, can be handled in the open air, no inert gas line needed, although it would be nice if it could reduce those pesky aliphatic nitro groups. For the phenylnitropropenes like P2NP, it can be used in a two step reduction to amphetamines however, first reducing the double bond of the nitroalkene, before extraction of the nitroalkene and reduction of the nitro group using iron dust in glacial acetic acid with a tad of ferric chloride added to coordinate as a lewis acid/base pair to the nitro group, and allow a greater ease of reduction. If done on the nitropropenes without reduction of the double bond, it gives the ketone instead, P2P/phenylacetone, which can be reductively aminated by forming an imine with an alkylamine such as methylamine, ethylamine for methylated or N-ethyl amphetamines respectively, using molecular sieves to protect the imine by abstraction of the water formed so the imine isn't hydrolyzed, then borohydride can reduce the imine to the amine.
Or else P2P ketoxime can be used for primary amine amphetamines, via the Bouveault-Blanc reduction, using a solution of the ketoxime in absolute anhydrous ethanol, under inert gas, whilst little chips of sodium metal are added, to reduce the ketoxime to the primary amine (amphetamine itself, in that case)
So even though it won't reduce the nitroalkene to the aminoalkane directly, borohydride still has its uses there, and for psychedelic phenethylamines/psychedelic ring-substituted amphetamines too.
Glad the dog is well odeon.
