Benzyl potassium

Names
Other names

Potassium benzyl

Identifiers

CAS Number

* 2785-29-7

3D model (JSmol)

* Interactive image

ChemSpider |

* 10675000

PubChem CID

* 11083915

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
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

Tracking categories (test):

* SizeSet

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]

(CH

2Hg + 2 K → 2 CH

4K + Hg

4K → KCH

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

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.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Benzyl potassium. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Benzyl_potassium&oldid=4243254"
*[CID]: Compound ID