Benzyl potassium

Benzyl potassium
Names
Other names Potassium benzyl
Identifiers
CAS Number	2785-29-7
3D model (JSmol)	Interactive image
ChemSpider	10675000
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
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:^[1]

(CH₃C₆H₄)₂Hg + 2 K → 2 CH₃C₆H₄K + Hg

CH₃C₆H₄K → KCH₂C₆H₅

A modern synthesis involves the reaction of butyllithium, potassium tert-butoxide, and toluene.^[2] 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.

References

↑ Gilman, Henry; Pacevitz, Henry A.; Baine, Ogden "Benzylalkali Compounds" Journal of the American Chemical Society 1940, vol. 62, pp. 1514-20. doi:10.1021/ja01863a054
↑ L. Lochmann, J. Trekoval, Lithium-potassium exchange in alkyllithium/potassium t-pentoxide systems: XIV. Interactions of alkoxides, Journal of Organometallic Chemistry Volume 326, Issue 1, 26 May 1987, Pages 1-7 doi:10.1016/0022-328X(87)80117-1

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