Benzyl potassium

Benzyl potassium

Names
Other names Potassium benzyl
Identifiers
CAS Number	2785-29-7
3D model (JSmol)	Interactive image
ChemSpider	10675000
CompTox Dashboard (EPA)	DTXSID00454524
InChI InChI=1S/C7H7.K/c1-7-5-3-2-4-6-7;/h2-6H,1H2; Key: OQLLVOGBAKFMIS-UHFFFAOYSA-N InChI=1/C7H7.K/c1-7-5-3-2-4-6-7;/h2-6H,1H2;/rC7H7K/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: OQLLVOGBAKFMIS-QPGMTJJQAI
SMILES [K]Cc1ccccc1
Properties
Chemical formula	C7H7K
Molar mass	130.23
Appearance	orange solid
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	ignites in air
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Benzyl potassium is an organopotassium compound with the formula C₆H₅CH₂K. It is an orange solid that is so extremely basic that it is compatible only with hydrocarbon solvents.

Synthesis

One early synthesis proceeds by two-step transmetallation reaction via p-tolylpotassium:

(CH₃C₆H₄)₂Hg + 2 K → 2 CH₃C₆H₄K + Hg

CH₃C₆H₄K → KCH₂C₆H₅

A modern synthesis involves the reaction of butyllithium, potassium tert-butoxide, and toluene. Although potassium hydride can also be used as a strong base for preparing potassium salts, benzyl potassium has the advantage of being molecular and hence more fast-acting.