Phenyllithium

Phenyllithium
	Kekulé, skeletal formula of phenyllithium
Names
	Systematic IUPAC name Phenyllithium
	Other names Lithiobenzene
Identifiers
CAS Number	591-51-5 ;
3D model (JSmol)	Interactive image;
Abbreviations	PhLi; LiPh
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;
UNII	9R6M9UV6QM ;
CompTox Dashboard (EPA)	DTXSID70938503 DTXSID20883453, DTXSID70938503 ;
	InChI InChI=1S/C6H5.Li/c1-2-4-6-5-3-1;/h1-5H; Key: NHKJPPKXDNZFBJ-UHFFFAOYSA-N ;
	SMILES [Li]c1ccccc1;
Properties
Chemical formula	C6H5Li
Molar mass	84.05 g·mol−1
Appearance	Colorless crystals
Density	0.828 g/cm3
Boiling point	140 to 143 °C (284 to 289 °F; 413 to 416 K)
Solubility in water	Reacts
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	48.3 to 52.5 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H250, H261, H302, H312, H314, H332
Precautionary statements	P210, P222, P231+P232, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P334, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P402+P404, P403+P235, P405, P422, P501 Preview warning: Omit Rules: keep P260, omit P261
Safety data sheet (SDS)	External MSDS
Related compounds
Related compounds	Phenylsodium; Phenylcopper;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Phenyllithium 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.