Potassium bis(trimethylsilyl)amide

Potassium bis(trimethylsilyl)amide
Names
	Preferred IUPAC name Potassium 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide
	Other names Potassium hexamethyldisilazide Potassium hexamethylsilazane
Identifiers
CAS Number	40949-94-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	KHMDS
ChemSpider	21171158 ;
PubChem CID	3251421;
UN number	3263
	InChI InChI=1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1 Key: IUBQJLUDMLPAGT-UHFFFAOYSA-N ;
	SMILES C[Si](C)(C)N([K])[Si](C)(C)C;
Properties
Chemical formula	KSi2C6NH18
Molar mass	199.4831 g mol−1
Appearance	White, opaque crystals
Solubility in water	Reacts
Hazards
GHS pictograms
GHS Signal word	DANGER
GHS hazard statements	H314
GHS precautionary statements	P280, P305+351+338, P310
Related compounds
Other cations	Lithium bis(trimethylsilyl)amide; Sodium 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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	Infobox references

Potassium bis(trimethylsilyl)amide (commonly abbreviated as KHMDS, Potassium(K) HexaMethylDiSilazide) or potassium hexamethyldisilazane^[1] is the chemical compound with the formula ((CH₃)₃Si)₂NK. It is a strong, non-nucleophilic base with an approximate pK_a of 26 (compare to lithium diisopropylamide, at 36).^{[citation needed]}

Structure

In the solid state, the unsolvated compound is dimeric, with two potassium and two nitrogen atoms forming a square. This compound is soluble in hydrocarbon solvents and conducts electricity poorly in solution and in the melt. This is attributed to very strong ion pairing.^[3]