METHYLLITHIUM

Base Information

• Chemical Name: METHYLLITHIUM
• CAS No.: 917-54-4
• Deprecated CAS: 12540-68-0,33825-29-5,33825-29-5
• Molecular Formula: CH3Li
• Molecular Weight: 21.9758
• Hs Code.: 29319090
• European Community (EC) Number: 213-026-4
• DSSTox Substance ID: DTXSID7061273
• Wikipedia: Methyllithium
• Wikidata: Q413849
• Mol file: 917-54-4.mol

Synonyms:Lithiummethide;

Chemical Property of METHYLLITHIUM

Chemical Property:

• Appearance/Colour: colorless to yellowish solution
• Melting Point: 70-71oC
• Boiling Point: 35oC
• Flash Point: 5°F
• PSA: 0.00000
• Density: 0.85 g/mL at 20 °C
• LogP: 0.58380
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 22.03947853
• Heavy Atom Count: 2
• Complexity: 2

Purity/Quality:

99% ^*data from raw suppliers

Methyllithium(1.6MinDiethylEther) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+,C,N,F
• Hazard Codes: F+,C,N,F,Xn,Xi
• Statements: 12-15-17-22-34-66-67-65-51/53-11-36/37/38-36/38-19-40-36/37-37-14/15
• Safety Statements: 16-26-36/37/39-45-43-30-60-62-61-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metals, Organic Compounds
• Canonical SMILES: [Li+].[CH3-]
• Uses: There are no significant industrial uses of methyllithium, but it is widely used in the laboratory in Grignard type reactions. Methyllithium is an organolithium reagent mainly used for deprotonation and as a source of methyl anion. It is a strong base and a strong nucleophile. Methyllithium lithium bromide complex solution (MeLi.LiBr) can be used as a methylating agent for the α-methylation of alkoxyaryl ketones.

Technology Process of METHYLLITHIUM

There total 36 articles about METHYLLITHIUM which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

methyl bromide (74-83-9) + lithium (7439-93-2) → methyllithium (917-54-4)

Guidance literature:

In formaldehyde diethyl acetal; at 10 - 30 ℃; for 2.5 - 7.5h;

Reference yield: 86.0%

4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone (65457-77-4) → methyllithium (917-54-4) + (1S,4S)-1-Methyl-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enol (99474-57-4,99474-58-5,114790-76-0)

Guidance literature:

In tetrahydrofuran; at -30 ℃; for 1h;

DOI:10.1016/S0040-4039(00)89245-X

Reference yield: 83.0%

methyl iodide (74-88-4) → methyllithium (917-54-4)

Guidance literature:

With n-butyllithium; In hexane; dichloromethane; at -40 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1080/10426507.2020.1712395

upstream raw materials:

methyl bromide

methylene chloride

ethyllithium

dimethylmercury

Downstream raw materials:

2,3,5-trimethylpyrazine

1-(1-hydroxycyclohexyl)ethan-1-one

2-(1-hydroxycyclohexyl)propan-2-ol

2-phenoxy-5-bromobenzoic acid

Refernces

• 1、 Gilman,Gaj. "-". . p. 1165,1168. Retrieved 1957.
• 2、 Brown,Rogers. "-". . p. 1859. Retrieved 1957.
• 3、 Stewart, Joanne L.,Andersen, Richard A.. "Preparation and Crystal Structure of the Addition Compound MeLi*U4, a Compound with a Uranium to Carbon ?-Bond". . p. 1846 - 1847. Retrieved 1987.
• 4、 Neumeier, Maria,Gschwind, Ruth M.. "Elongated Gilman cuprates: The key to different reactivities of cyano- and iodocuprates". . p. 5765 - 5772. Retrieved 2014/05/06.