Sodium bis(trimethylsilyl)amide

Sodium bis(trimethylsilyl)amide
Names
Preferred IUPAC name
Sodium 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide
Other names
Sodium hexamethyldisilazide
Sodium hexamethyldisilazane
Identifiers
3D model (JSmol)
Abbreviations NaHMDS
3629917
ChemSpider
ECHA InfoCard 100.012.713 Edit this at Wikidata
EC Number
  • 213-983-8
UN number 3263
  • InChI=1S/C6H18NSi2.Na/c1-8(2,3)7-
    9(4,5)6;/h1-6H3;/q-1;+1 ☒N
    Key: WRIKHQLVHPKCJU-UHFFFAOYSA-N checkY
  • InChI=1/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1/rC6H18NNaSi2/c1-9(2,3)7(8)10(4,5)6/h1-6H3
    Key: WRIKHQLVHPKCJU-JSJAVMDOAQ
  • InChI=1S/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
    Key: WRIKHQLVHPKCJU-UHFFFAOYSA-N
  • C[Si](C)(C)N([Na])[Si](C)(C)C
Properties
NaN(Si(CH3)3)2
Molar mass 183.377 g·mol−1
Appearance off-white solid
Density 0.9 g/cm3, solid
Melting point 171 to 175 °C (340 to 347 °F; 444 to 448 K)
Boiling point 202 °C (396 °F; 475 K) 2 mmHg
Reacts with water
Solubility in other solvents THF, benzene
toluene
Structure
Triangular pyramidal
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly flammable, corrosive
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H312, H314, H332, H412
P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P405, P501
Related compounds
Other cations
 Lithium bis(trimethylsilyl)amide
(LiHMDS)
Potassium bis(trimethylsilyl)amide
Related compounds
 Lithium diisopropylamide (LDA)
Sodium hydride
Potassium hydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula NaN(Si(CH3)3)2. This species, usually called NaHMDS (sodium hexamethyldisilazide), is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether, but also in aromatic solvents, like benzene and toluene by virtue of the lipophilic TMS groups.[1]

NaHMDS is quickly destroyed by water to form sodium hydroxide and bis(trimethylsilyl)amine.

  1. ^ Watson, B. T.; Lebel, H. "Sodium bis(trimethylsilyl)amide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.rs071m.pub2