Sodium hydride

It is an ionic material that is insoluble in all solvents (other than molten sodium metal), consistent with the fact that H− ions do not exist in solution.

[10] Industrially, NaH is prepared by introducing molten sodium into mineral oil with hydrogen at atmospheric pressure and mixed vigorously at ~8000 rpm.

Typical "easy" substrates contain O-H, N-H, S-H bonds, including alcohols, phenols, pyrazoles, and thiols.

[13] Notably boron trifluoride reacts to give diborane and sodium fluoride:[14] Si–Si and S–S bonds in disilanes and disulfides are also reduced.

The compound is often used in this form but the pure grey solid can be prepared by rinsing the commercial product with pentane or tetrahydrofuran, with care being taken because the waste solvent will contain traces of NaH and can ignite in air.

It also reacts vigorously with water or humid air to release hydrogen, which is very flammable, and sodium hydroxide (NaOH), a quite corrosive base.

In practice, most sodium hydride is sold as a dispersion in mineral oil, which can be safely handled in air.

[17] Although sodium hydride is widely used in DMSO, DMF or DMAc for SN2 type reactions there have been many cases of fires and/or explosions from such mixtures.

Sodium hydride
Sodium hydride
Space-filling model of part of the crystal structure of sodium hydride
Space-filling model of part of the crystal structure of sodium hydride
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid