[Products Name] Sodium-Hydride
[Molecular Formula] NaH
[CAS No.] 7646-69-7
[Product Description]
Sodium hydride is the chemical compound with the formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H? ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water.
It is an ionic material that is insoluble in organic solvents (although apparently soluble in molten Na), consistent with the fact that H? remains an unknown anion in solution. Because of the insolubility of NaH, all reactions involving NaH occur at the surface of the solid.
[Properties]
mp 800 °C (dec.)(lit.)
density 1.2
Fp 185°C
storage temp. Store at RT.
form powder (moistened with oil)
Water Solubility REACTS
Sensitive Air & Moisture Sensitive
[Application]
·As a strong base
First and foremost, NaH is a base of wide scope and utility in organic chemistry.[3] It is capable of deprotonating a range of even weak Br?nsted acids to give the corresponding sodium derivatives. Typical "easy" substrates contain O-H, N-H, S-H bonds, including alcohols, phenols, pyrazoles, and thiols.
NaH most notably is employed to deprotonate carbon acids such as 1,3-dicarbonyls and analogues such as malonic esters. The resulting sodium derivatives can be alkylated. NaH is widely used to promote condensation reactions of carbonyl compounds via the Dieckmann condensation, Stobbe condensation, Darzens condensation, and Claisen condensation. Other carbon acids susceptible to deprotonation by NaH include sulfonium salts and DMSO. NaH is used to make sulfur ylides, which in turn are used to convert ketones into epoxides.
·As a reducing agent
NaH reduces certain main group compounds, but analogous reactivity is unknown in organic chemistry. Notably boron trifluoride reacts to give diborane and sodium fluoride：
6 NaH + 2 BF3 → B2H6 + 6 NaF
Si-Si and S-S bonds in disilanes and disulfides are also reduced.
·Drying agent
Because of its rapid and irreversible reaction with water, NaH can be used to dry some organic solvents. Other drying agents are far more widely used, such as calcium hydride.
