Benzyl potassium: Difference between revisions
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The main image on the page incorrectly showed phenylethyl potassium instead of benzyl potassium, I made a new image that shows benzyl potassium and uploaded it. |
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| OtherNames = Potassium benzyl |
| OtherNames = Potassium benzyl |
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| CASNo = 2785-29-7 |
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Revision as of 07:23, 23 January 2018
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| Names | |
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| Other names
Potassium benzyl
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C7H7K | |
| Molar mass | 130.23 g/mol |
| Appearance | Orange solid |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Ignites in air |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 (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.