フェニルリチウム

解説

フェニルリチウム,ブロモベンゼンまたはヨードベンゼンに金属リチウムを作用させて得られる無色固体状の有機金属化合物。空気中ではきわめて不安定で，瞬時に発火して燃え尽きてしまう。エーテル類によく溶けるが，ベンゼンにはほとんど溶けない。フェニルグリニャール試薬とほぼ同じ反応性を示し，有機合成上重要な化合物である。

用途

有機合成用。

使用上の注意

不活性ガス封入

化学的特性

Phenyllithium is a colorless crystalline solid or dark brown to black solution, It is soluble in polar solvents such as ethers and tertiary amines but insoluble in hydrocarbons. Concentrated solutions in volatile solvents are pyrophoric but can be safely handled under inert atmosphere.

使用

Phenyllithium Solution (1.9M in Dibutyl Ether) is used as catalyst in the synthesis of pharmaceuticals. Used in the preparation of sulfonamides as well as in the preparation of orally bioavailable inhibitors of lipoprotein-associated phospholipase A2.

製造方法

Phenyllithium is usually prepared in the laboratory from bromobenzene and lithium metal in diethyl ether. Since phenyllithium cleaves ether, the solution must be used within a day or refrigerated. Industrially, it is produced from chlorobenzene and lithium metal dispersion in a benzene-ether mixture. A potentially useful and inexpensive process is one in which benzene is metalated by n-butyllithium in the presence of di-tertiary amines.