Phenyllithium

Phenyllithium
Kekulé, skeletal formula of phenyllithium
Names
Systematic IUPAC name
Phenyllithium[2]
Other names
Lithiobenzene[1]
Identifiers
3D model (JSmol)
Abbreviations LiPh, PhLi
506502
ChEBI
ChemSpider
ECHA InfoCard 100.008.838 Edit this at Wikidata
EC Number
  • 209-720-1
2849
MeSH phenyllithium
  • InChI=1S/C6H5.Li/c1-2-4-6-5-3-1;/h1-5H; ☒N
    Key: NHKJPPKXDNZFBJ-UHFFFAOYSA-N ☒N
  • [Li]c1ccccc1
Properties
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)
Reacts
Thermochemistry
48.3-52.5 kJ mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H226, H250, H261, H302, H312, H314, H332
P210, P222, P231+P232, P233, P240, P241, P242, P243, P260, P261, 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
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
 phenylcopper, phenylsodium, phenylcobalt
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[3] 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.[4]

  1. ^ Typically used to describe substituted derivatives. See, e.g., Katsutoshi Kobayashi; Soichi Sato; Horn, Ernst; Naomichi Furukawa (1998), "First isolation and characterization of sulfenium cation salts stabilized by the coordination of two nitrogen atoms," Tetrahedron Letters, 39: 17, pp. 2593-2596. ISSN 0040-4039. DOI 10.1016/S0040-4039(98)00277-9.
  2. ^ "phenyllithium (CHEBI:51470)". Chemical Entities of Biological Interest (ChEBI). Cambridge, UK: European Bioinformatics Institute. 2009-01-22. Main. Retrieved 2013-06-01.
  3. ^ Wietelmann, U.; Bauer, R. J. "Lithium and Lithium Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_393. ISBN 978-3527306732.
  4. ^ Gilman, H.; Zoellner, E. A.; Selby, W. M. (1932). "An Improved Procedure for the Preparation of Organolithium Compounds". Journal of the American Chemical Society. 54 (5): 1957–1962. doi:10.1021/ja01344a033.