// Workers AI · dad joke modeIs benzyl potassium a good date? It bonds well.

Benzyl potassium
Names
	Other names Potassium benzyl
Identifiers
CAS Number	2785-29-7;
3D model (JSmol)	Interactive image;
ChemSpider	10675000;
PubChem CID	11083915;
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	130.231 g·mol−1
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

Benzylpotassium is an organopotassium compound with the formula C₆H₅CH₂K, an orange powder. Like organo-alkali metal reagents in general, benzyl potassium is highly reactive, so much so that it reacts with most solvents. It is highly air sensitive.

Synthesis

One early synthesis proceeds by two-step transmetallation reaction by 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]

The structure of the related diphenylmethane derivative has been confirmed by X-ray crystallography.^[3]

References

↑ Gilman, Henry; Pacevitz, Henry A; Baine, Ogden (1940). "Benzylalkali Compounds1". Journal of the American Chemical Society. 62 (6): 1514. doi:10.1021/ja01863a054.
↑ Lochmann, L; Trekoval, J (1987). "Lithium-potassium exchange in alkyllithium/potassium t-pentoxide systems". Journal of Organometallic Chemistry. 326: 1. doi:10.1016/0022-328X(87)80117-1.
↑ Schumann, Herbert; Freckmann, Dominique M. M.; Dechert, Sebastian (2006). "Organometallic Compounds of the Lanthanides. 179. Synthesis and Structural Characterization of a Mixed Alkyl (Benzhydryl, Trimethylsilylmethyl) Lutetium Complex". Organometallics. 25 (10): 2696–2699. doi:10.1021/om0601201.

[1] Gilman, Henry; Pacevitz, Henry A; Baine, Ogden (1940). "Benzylalkali Compounds1". Journal of the American Chemical Society. 62 (6): 1514. doi:10.1021/ja01863a054.

[2] Lochmann, L; Trekoval, J (1987). "Lithium-potassium exchange in alkyllithium/potassium t-pentoxide systems". Journal of Organometallic Chemistry. 326: 1. doi:10.1016/0022-328X(87)80117-1.

[3] Schumann, Herbert; Freckmann, Dominique M. M.; Dechert, Sebastian (2006). "Organometallic Compounds of the Lanthanides. 179. Synthesis and Structural Characterization of a Mixed Alkyl (Benzhydryl, Trimethylsilylmethyl) Lutetium Complex". Organometallics. 25 (10): 2696–2699. doi:10.1021/om0601201.

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