Phenyllithium

Synonym(s):PhLi

CAS NO.：591-51-5
Empirical Formula: C6H5Li
Molecular Weight: 84.05
MDL number: MFCD00014254
EINECS: 209-720-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-22 14:21:17

What is Phenyllithium?

Chemical properties

Phenyllithium is a colorless crystalline solid or dark brown to black solution, It is soluble in polar solvents such as ethers and tertiary amines but insoluble in hydrocarbons. Concentrated solutions in volatile solvents are pyrophoric but can be safely handled under inert atmosphere.

The Uses of Phenyllithium

Phenyllithium Solution (1.9M in Dibutyl Ether) is used as catalyst in the synthesis of pharmaceuticals. Used in the preparation of sulfonamides as well as in the preparation of orally bioavailable inhibitors of lipoprotein-associated phospholipase A2.

Preparation

Phenyllithium is usually prepared in the laboratory from bromobenzene and lithium metal in diethyl ether. Since phenyllithium cleaves ether, the solution must be used within a day or refrigerated. Industrially, it is produced from chlorobenzene and lithium metal dispersion in a benzene-ether mixture. A potentially useful and inexpensive process is one in which benzene is metalated by n-butyllithium in the presence of di-tertiary amines.

Definition

ChEBI: Phenyllithium is an aryllithium compound.

Properties of Phenyllithium

Melting point:	160-163 °C(Solv: benzene (71-43-2))
Boiling point:	140-143 °C
Density	0.835 g/mL at 25 °C
Flash point:	20 °C
storage temp.	Store at +2°C to +8°C.
solubility	Miscible with ether and hydrocarbons.
form	Dark Brown Solution
Water Solubility	Severe reaction
Sensitive	Air & Moisture Sensitive
BRN	506502
Stability:	Moisture Sensitive
CAS DataBase Reference	591-51-5(CAS DataBase Reference)
EPA Substance Registry System	Lithium, phenyl- (591-51-5)

Safety information for Phenyllithium

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H226:Flammable liquids H314:Skin corrosion/irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.