Sodium bis(trimethylsilyl)amide
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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]
Quick Facts Names, Identifiers ...
Names | |
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Preferred IUPAC name
Sodium 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide | |
Other names
Sodium hexamethyldisilazide Sodium hexamethyldisilazane | |
Identifiers | |
3D model (JSmol) |
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Abbreviations | NaHMDS |
3629917 | |
ChemSpider |
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ECHA InfoCard | 100.012.713 |
EC Number |
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PubChem CID |
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UN number | 3263 |
CompTox Dashboard (EPA) |
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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 | 170 °C (338 °F; 443 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: | |
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).
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NaHMDS is quickly destroyed by water to form sodium hydroxide and bis(trimethylsilyl)amine.