Phenyllithium

Basic Information

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CAS Number

591-51-5

Molecular Formula

C6H5Li

Molecular Weight

84.05 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Hydrocarbons

Basic Physical Properties

Boiling Point

140-143 ºC

Flash Point

20 ºC

Solubility

Miscible with ether and hydrocarbons.

SMILES

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[Li+].C1=CC=[C-]C=C1

InChI

InChI=1S/C6H5.Li/c1-2-4-6-5-3-1;/h1-5H;

InChIKey

NHKJPPKXDNZFBJ-UHFFFAOYSA-N

LogP

0.48040000000000005

Topological Polar Surface Area

0.0 Å²

Hydrogen Bond Donor/Acceptor

0 / 0

Complexity

95.8

Safety Information

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GHS Hazard Pictograms

H315

H319

H335

H412

Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

H412 Harmful to aquatic life with long lasting effects
Hazardous to the aquatic environment, long-term hazard

Hazard Class

Class 4.3 Class 4.3

Sensitiveness

Air & Moisture Sensitive

Synonyms & References

English

NS00080186
R-ALBUTEROLHYDROCHLORIDE
LiPh
Lithium, phenyl-
MFCD00014254
phenyl lithium
phenyl-lithium
Phenyllithium, typically 1.9M in di-n-butyl ether
lithium;benzene
NHKJPPKXDNZFBJ-UHFFFAOYSA-N
DTXSID70938503
CHEBI:51470
EC 209-720-1
DTXSID20883453
Lithium, diphenyldi-
lithium benzenide
591-51-5
Phenyllithium
17438-88-9
phenyl litium
P1429
FT-0689293
PhLi
AKOS015891301
EINECS 209-720-1
Q419478
phenyllithium
PHENYLLITHIUM 2.0M SOLUTION IN DIBUTYLETHER
Phenyllithium, 1.0 M solution in ethyl ether, SpcSeal
1.7M solution in THF, MkSeal
Lithiobenzene

MDL Number

MFCD00014254

FAQ

What are the physical and chemical properties of Phenyllithium (CAS: 591-51-5)?

Phenyllithium (CAS: 591-51-5) is a white crystalline solid at room temperature with a molecular weight of 101.15 g/mol. It is highly reactive and soluble in ether and alcohols. Phenyllithium is known for its strong basicity and nucleophilicity, making it an excellent reagent in nucleophilic substitution and addition reactions.

How is Phenyllithium (CAS: 591-51-5) typically synthesized?

Phenyllithium (CAS: 591-51-5) is typically synthesized by the reaction of phenylmagnesium bromide with lithium metal in a dry ether solvent. The reaction is highly exothermic and requires careful control to ensure a high yield and selectivity. Common procedures involve the use of a drying agent like magnesium sulfate to remove trace water, which could otherwise react with the phenyllithium to form phenoxide.

What industries use Phenyllithium (CAS: 591-51-5)?

Phenyllithium (CAS: 591-51-5) is widely used in the pharmaceutical industry for the synthesis of complex organic molecules and intermediates. It is also used in polymer synthesis to introduce functional groups, in the production of sensors, and in semiconductor fabrication processes for specific chemical reactions.

What precautions should be taken when handling Phenyllithium (CAS: 591-51-5)?

Handling Phenyllithium (CAS: 591-51-5) requires strict safety protocols. It is highly reactive and can spontaneously ignite in air. Proper personal protective equipment (PPE) such as gloves, goggles, and a lab coat is essential. Work should be conducted in a fume hood. In case of a spill, it should be carefully contained and disposed of according to safety data sheet (SDS) guidelines.