Phenyl lithium

Phenyllithium

Names
Systematic IUPAC name Phenyllithium
Other names Phenyl lithium
Identifiers
CAS Number	591-51-5 Y
3D model (JSmol)	Interactive image
Abbreviations	LiPh, PhLi
Beilstein Reference	506502
ChEBI	CHEBI:51470
ChemSpider	10254416
ECHA InfoCard	100.008.838
EC Number	209-720-1
Gmelin Reference	2849
MeSH	phenyllithium
PubChem CID	637932
InChI InChI=1S/C6H5.Li/c1-2-4-6-5-3-1;/h1-5H;  Key: NHKJPPKXDNZFBJ-UHFFFAOYSA-N
SMILES [Li]c1ccccc1
Properties
Chemical formula	LiC 6H 5
Molar mass	84.045 g mol−1
Appearance	Colorless crystals
Density	828 mg cm−3
Boiling point	140 to 143 °C (284 to 289 °F; 413 to 416 K)
Solubility in water	Reacts
Thermochemistry
Std enthalpy of formation (ΔfHo298)	48.3-52.5 kJ mol−1
Hazards
Safety data sheet	External MSDS
R-phrases (outdated)	R14, R17, R23/24/25, R48
S-phrases (outdated)	(S1/2), S8, S9, S16, S26, S30, S46, S36/37/39, S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
(what is Y ?)
Infobox references

Phenyllithium or lithobenzene is an organometallic agent with the empirical formula C₆H₅Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyllithium is colorless; however, solutions of phenyllithium are various shades of brown or red depending on the solvent used and the impurities present in the solute.

Phenyllithium is an organolithium compound that forms monoclinic crystals. Solid phenyllithium can be described as consisting of dimeric Li₂Ph₂ subunits. The Li atoms and the ipso carbons of the phenyl rings form a planar four-membered ring. The plane of the phenyl groups are perpendicular to the plane of this Li₂C₂ ring. Additional strong intermolecular bonding occurs between these phenyllithium dimers and the π-electrons of the phenyl groups in the adjacent dimers, resulting in an infinite polymeric ladder structure.

In solution, it takes a variety of structures dependent on the organic solvent. In tetrahydrofuran, it equilibrates between monomer and dimer states. In ether, as it is commonly sold, phenyllithium exists as a tetramer. Four Li atoms and four ipso carbon centers occupy alternating vertices of a distorted cube. Phenyl groups are at the faces of the tetrahedron and bind to three of the nearest Li atoms.