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45770 Phenyllithium, typically 1.9M in di-n-butyl ether

CAS Number
591-51-5
Synonyms

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Bulk/Specialty

Phenyllithium, typically 1.9M in di-n-butyl ether

MDL
MFCD00014254
EINECS
209-720-1

Chemical Properties

Formula
C6H5Li
Formula Weight
84.05
Form
Liquid
Boiling Point
140-143°
Flash Point
25°(77°F)
Density
0.81
Storage & Sensitivity
Moisture Sensitive. Air Sensitive. May form a Precipitate. Store under Argon. Ambient temperatures.
Solubility
Miscible with ether and hydrocarbons.

Applications

Phenyllithium is used as an alkylating agent to facilitate the formation of carbon-carbon bonds by nucleophilic addition and substitution reactions. It is used in the preparation of 2-phenylpyridine by reacting with pyridine. It acts as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic synthesis.

Notes

Air sensitive. Store in cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents, alcohols and acids. Reacts violently with water, oxygen, alcohols and acids.

Literature References

Bohler, B.; Gunther, H. The Aggregation Behavior of Butyllithium in Diethyl Ether in the Presence of LiBr, LiClO4, and Phenyllithium: A Deuterium-Induced Secondary 6Li-NMR Isotope-Effect Study. Helv. Chim. Acta 2015, 98 (4), 427-446.

Kojima, T.; Hiraoka, S. Mesityllithium and p-(dimethylamino) phenyllithium for the selective alternate trilithiation of the hexaphenylbenzene framework. Chem. Commun. 2014, 50 (72), 10420-10423.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H303-H314-H318-H340-H350-H335

Flammable liquid and vapour. May be harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May cause genetic defects. May cause cancer. May cause respiratory irritation.

Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
506502
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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