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Lithium bis(trimethylsilyl)amide
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Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si(CH3)3)2. It is commonly abbreviated as LiHMDS or Li(HMDS) (lithium hexamethyldisilazide - a reference to its conjugate acid HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.
Quick Facts Names, Identifiers ...
![]() Monomer (does not exist) | |
![]() Cyclic trimer | |
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Names | |
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Preferred IUPAC name
Lithium 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide | |
Other names
Lithium hexamethyldisilazide Hexamethyldisilazane lithium salt | |
Identifiers | |
3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.021.569 ![]() |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
LiN(Si(CH3)3)2 | |
Molar mass | 167.33 g·mol−1 |
Appearance | White solid |
Density | 0.86 g/cm3 at 25 °C |
Melting point | 71 to 72 °C (160 to 162 °F; 344 to 345 K) |
Boiling point | 80 to 84 °C (176 to 183 °F; 353 to 357 K) (0.001 mm Hg) |
decomposes | |
Solubility | Most aprotic solvents THF, hexane, toluene |
Acidity (pKa) | 26 |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
flammable, corrosive |
Related compounds | |
Related compounds |
Sodium bis(trimethylsilyl)amide Potassium bis(trimethylsilyl)amide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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