Lithium bis(trimethylsilyl)amide

Lithium bis(trimethylsilyl)amide

Monomer (does not exist)
Cyclic trimer
Names
Preferred IUPAC name Lithium 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide
Other names Lithium hexamethyldisilazide Hexamethyldisilazane lithium salt
Identifiers
CAS Number	4039-32-1 Y
3D model (JSmol)	ionic monomer: Interactive image cyclic trimer: Interactive image
ChemSpider	21170111 N
ECHA InfoCard	100.021.569
PubChem CID	2733832
UNII	RC4N1I108M Y
CompTox Dashboard (EPA)	DTXSID2044426
InChI InChI=1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
SMILES ionic monomer: C[Si](C)(C)[N-][Si](C)(C)C.[Li+] cyclic trimer: C[Si](C)(C)[N+]0([Si](C)(C)C)[Li-][N+]([Si](C)(C)C)([Si](C)(C)C)[Li-][N+]([Si](C)(C)C)([Si](C)(C)C)[Li-]0
Properties
Chemical formula	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)
Solubility in water	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). N verify (what is YN ?) Infobox references

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.