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Cas Database |
| Name |
METHYLLITHIUM |
EINECS | 213-026-4 |
| CAS No. | 917-54-4 | Density | 0.85 g/mL at 20 °C |
| PSA | 0.00000 | LogP | 0.58380 |
| Solubility | Reacts with water. | Melting Point |
70-71oC |
| Formula | CH3Li | Boiling Point | 35oC |
| Molecular Weight | 21.9758 | Flash Point | 5°F |
| Transport Information | UN 3399 4.3/PG 1 | Appearance | colorless to yellowish solution |
| Safety | 16-26-36/37/39-45-43-30-60 | Risk Codes | 12-15-17-22-34-66-67-65-51/53-11 |
| Molecular Structure |
|
Hazard Symbols |
 F+, C, N, F
|
| Synonyms |
Lithiummethide; |
Article Data | 43 |
METHYLLITHIUM Synthetic route
| Conditions | Yield |
|---|---|
| In formaldehyde diethyl acetal at 10 - 30℃; for 2.5 - 7.5h; | 91% |
| reaction at -40°C;; |
- 65457-77-4
4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone
A
- 917-54-4
methyllithium
- 99474-57-4, 99474-58-5, 114790-76-0
(1S,4S)-1-Methyl-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enol
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -30℃; for 1h; | A 86% B 6% |
| Conditions | Yield |
|---|---|
| With n-butyllithium In hexane; dichloromethane at -40 - 20℃; for 1h; Inert atmosphere; | 83% |
| With diethyl ether; lithium | |
| With lithium |
- 109-72-8, 29786-93-4
n-butyllithium
- 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
A
- 917-54-4
methyllithium
B
- 75934-66-6
pentamethylpentylbenzene
| Conditions | Yield |
|---|---|
| With N,N,N,N,-tetramethylethylenediamine In Cyclopentane at 55℃; for 5.5h; | A n/a B 77% |
- 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
- 594-19-4
tert.-butyl lithium
A
- 917-54-4
methyllithium
B
- 56909-25-2
2,3,4,5,6-pentamethylneopentylbenzene
| Conditions | Yield |
|---|---|
| In cyclohexane at 88℃; for 3.3h; | A n/a B 63% |
| Conditions | Yield |
|---|---|
| With lithium |
| Conditions | Yield |
|---|---|
| With bromobenzene; diethyl ether; lithium | |
| With iodobenzene; diethyl ether; lithium | |
| With lithium |
| Conditions | Yield |
|---|---|
| With Petroleum ether |
METHYLLITHIUM Chemical Properties
This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used as a solution in ethers, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium(917-54-4) require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium(917-54-4) is usually not prepared, but purchased as a solution in various ethers.
The density of methyllithium(917-54-4) is 0.85 g/mL at 20 °C and it has a flash point of 5 °F.
The molecular structure of methyllithium(917-54-4):
METHYLLITHIUM Production
2 Li + MeBr → LiMe + LiBr
The lithium bromide forms a complex with the methyllithium(917-54-4). Most commercially available methyllithium(917-54-4) consists of this complex. "Halide-free" methyllithium(917-54-4) is prepared from methyl chloride. Lithium chloride precipitates from the diethyl ether since it does not form a strong complex with methyllithium(917-54-4). The filtrate consists of fairly pure methyllithium(917-54-4).
METHYLLITHIUM Safety Profile
METHYLLITHIUM Specification
Bonding
These clusters are considered "electron-deficient," that is, they do not follow the octet rule because the molecules lack sufficient electrons to form four 2-centered, 2-electron bonds around each carbon atom, in contrast to most organic compounds. The hexamer is a 30 electron compound (30 valence electrons.) If one allocates 18 electrons for the strong C-H bonds, 12 electrons remain for Li-C and Li-Li bonding. There are six electrons for six metal-metal bonds and one electron per methyl-η3 lithium interaction.
The strength of the C-Li bond has been estimated at around 57 kcal/mol from IR spectroscopic measurements.
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