Sodium cyclopentadienide
Sodium cyclopentadienide
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Sodium cyclopentadienide

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Sodium cyclopentadienide

Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp is the cyclopentadienide anion. Sodium cyclopentadienide is a colorless solid, although samples often are pink owing to traces of oxidized impurities.

The first salt of cyclopentadienide to be reported was potassium cyclopentadienide, prepared by Johannes Thiele. In 1901 there was not much interest in the topic.

Sodium cyclopentadienyl is prepared from cyclopentadiene and molten sodium metal: Sodium can also be provided as "sodium wire" or "sodium sand", the fine suspension produced when molten sodium is mixed with refluxing xylene, then cooled. The highly exothermic metallation can undergo catastrophic thermal runaway without proper cooling, as occurred in the T2 Laboratories explosion and fire.

Alternatively, many reagents deprotonate cyclopentadiene; it has pKa 15. Early work used Grignard reagents as bases, but sodium hydride is more convenient nowadays:

Sodium cyclopentadienide is commercially available as a solution in THF.

Sodium cyclopentadienide is a common reagent for the preparation of metallocenes. For example, the preparation of ferrocene and zirconocene dichloride:

Sodium cyclopentadienide is also used for the preparation of substituted cyclopentadienyl derivatives such as the ester and formyl derivatives:

These compounds are used to prepare substituted metallocenes such as 1,1'-ferrocenedicarboxylic acid.

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