| Identification | More | [Name]
Phenyllithium | [CAS]
591-51-5 | [Synonyms]
LITHIUMPHENYL
PHENYLLITHIUM
PHENYLLITHIUM DIBUTYL
PHLI
phenyl-lithiu
PHENYLLITHIUM, 1.9M SOLUTION IN CYCLO-HEXANE-ETHER, 70 TO 30
PHENYLLITHIUM SOLUTION 20% IN DIBUTYLETHER
PHENYLLITHIUM SOL., 1.8-2.1 M IN CYCLO-HEXANE/ETHER 70/30%
PHENYLLITHIUM, CA. 1.8M SOLUTION IN DI-N-BUTYLETHER
20%solutioninDibutylether
Phenyllithium, 2.0M solution (20%) in dibutylether
phenyllithium solution
phenyllithium, 1.5-1.7m in cyclohexane/ether
PHENYLLITHIUM(CA.17%INCYCLOHEXANE-DIETHYLETHER)
PHENYLLITHIUM, 2M SOLUTION IN CYCLOHEXANE/ETHER, 70/30
Phenyllithium, 1.5-1.7M in cyclohexane/ether, 70:30%, packaged under Argon in resealable ChemSealTM bottles
Phenyllithium, 1.5-1.7M in cyclohexane/ether, 70:30%
Phenyllithium (ca. 19% in Butyl Ether, ca. 1.9mol/L)
Phenyllithium, 1.5-1.7M in cyclohexane/ether, 70:30%, packaged under Argon in resealable ChemSeal bottles
Phenyllithium2.0M solution (20%) in dibutyletherAcroSeal§3 | [EINECS(EC#)]
209-720-1 | [Molecular Formula]
C14H23LiO | [MDL Number]
MFCD06200758 | [Molecular Weight]
214.27 | [MOL File]
591-51-5.mol |
| Chemical Properties | Back Directory | [Appearance]
dark brown to black solution | [Melting point ]
160-163 °C(Solv: benzene (71-43-2)) | [Boiling point ]
140-143 °C | [density ]
0.835 g/mL at 25 °C
| [Fp ]
20 °C
| [storage temp. ]
2-8°C
| [solubility ]
Miscible with ether and hydrocarbons. | [form ]
Dark Brown Solution | [Water Solubility ]
Severe reaction | [Sensitive ]
Air & Moisture Sensitive | [BRN ]
506502 | [Stability:]
Moisture Sensitive | [InChIKey]
NHKJPPKXDNZFBJ-UHFFFAOYSA-N | [CAS DataBase Reference]
591-51-5(CAS DataBase Reference) | [Storage Precautions]
Store under inert gas;Air sensitive;Moisture sensitive | [EPA Substance Registry System]
591-51-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,C,N | [Risk Statements ]
R11:Highly Flammable.
R14:Reacts violently with water.
R17:Spontaneously flammable in air.
R34:Causes burns.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R66:Repeated exposure may cause skin dryness or cracking.
R65:Harmful: May cause lung damage if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R22:Harmful if swallowed.
R19:May form explosive peroxides. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S60:This material and/or its container must be disposed of as hazardous waste .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S16:Keep away from sources of ignition-No smoking .
S6:Keep under ... (inert gas to be specified by the manufacturer) . | [RIDADR ]
UN 3392 4.2/PG 1
| [WGK Germany ]
2
| [F ]
1-10 | [TSCA ]
Yes | [HazardClass ]
4.3 | [PackingGroup ]
II | [HS Code ]
29319090 |
| Questions And Answer | Back Directory | [Description]
Phenyllithium is an organometallic compound that is used as a nucleophile for substitution and addition reactions, and in the synthesis of organolithium building blocks through lithium-metalloid and metalation exchange reactions.
| [Properties]
Phenyllithium has a molecular weight of 84.046 g/mol, a monoisotopic mass of 84.055 g/mol and an exact mass of 84.055 g/mol. It has a heavy atom count of 7 and a complexity of 95.8.
Phenyllithium is soluble in ether solvents; it is soluble in hydrocarbon solvents especially through the addition of donor additives/solvents.
| [Uses]
Phenyllithium is used for synthetic purposes to introduce a phenyl group into a compound or for metalation reactions. It undergoes typical Grignard type reactions.
| [Preparation]
Phenyllithium is synthesized by reacting elemental lithium with bromobenzene and dissolving the resulting products in ether. 18g[2.57 mol] of lithium that contains about 1-3% of sodium is flattened out using a hammer to attain a thickness of about 1.5 mm and then it is cut into chips of about 2x10x1.5 mm. The chips are placed into a flask holding 800 ml of anhydrous diethyl ether. The air is purged with dry argon or dry nitrogen and the ether is condensed to -250 C in the first two minutes of the reaction.
150.7 g of bromobenzene is placed into the flask through the dropping funnel, where one portion contains only 10 g of bromobenzene. After a few minutes of the reaction, there is a significant rise in temperature and the contents of the flask appear turbid. When the reaction starts to subside, after about 10 minutes, the remaining bromobenzene is added gradually to the flask using a dropper over a period of 1 hour, while maintaining the temperature of the contents between -150 C and -200 C. The dark coating on the lithium metal subsides almost entirely leaving behind a silver-like appearance.
Once all the bromobenzene is added to the flask, the contents are stirred and the temperature is maintained at -150 C for 1 hour. The temperature should then be allowed to increase up to 00, which will also be indicated a gradually fading glow of the reacting metal.
The resulting solution is emptied into a storage flask that has been filled with an inert gas. The filtration of the solution should take place in an inert atmosphere where a steady stream of argon or nitrogen[2-3 l/min] is passed through the reaction contents to prevent the solution from oxidation. Diethyl ether is then added to increase the Volume of the solution to 1 litre. The contents of the flask are then swirled gently[homogenization] to allow for the final step of the reaction, where the concentration is determined.
Solutions containing Phenyllithium are unstable at room temperature when left for long periods of time. The gradual attack of Phenyllithium on ethyl ether makes the commercial preparation of the compound undesirable. The incorporation of small quantities of ethyl ether to attain solutions of 1:1 phenyllithiumzethyl etherate complex in the presence of benzene reduces the average titer of the ethyl ether hence it makes the solution more stable.
The average titer should be about 1 molar, which corresponds to a high yield[90%] and purity. Amounts that are significantly higher or lower than the mol ratio often yield lesser amounts of Phenyllithium. The resulting 1:1 phenyllithiumzethyl etherate complex could be a tetramer or a dimer but it does not affect the ethyl ether to Phenyllithium ratio, which remains 1:1.
| [Application]
Phenyllithium can be used in the preparation of 1-Acetyl-1′-diphenylphosphinoferrocene from ferrocenophane
| [Hazard Statements]
Phenyllithium is a flammable liquid/vapour and it may catch fire when exposed to air. When it comes into contact with water it emits flammable gases. Phenyllithium may result in acute toxicity upon ingestion and inhalation, or when it comes into contact with one’s eyes and skin.
|
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: Phenyllithium is an aryllithium compound. |
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