Sodium bis (trimethylsilyl) amide

Structural formula
General
Surname	Sodium bis (trimethylsilyl) amide
other names	Sodium hexamethyldisilazide NaHMDS
Molecular formula	[(CH 3 ) 3 Si] 2 NNa
Brief description	white to light yellow solid
External identifiers / databases
CAS number 1070-89-9 EC number 213-983-8 ECHA InfoCard 100.012.713 PubChem 2724254 Wikidata Q2742490
properties
Molar mass	183.37 g mol −1
Physical state	firmly
Melting point	171-175 ° C
solubility	soluble in hexane , toluene and ether
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 314 P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sodium bis (trimethylsilyl) amide is a chemical compound from the group of trimethylsilylamides and the sodium salt of hexamethyldisilazane .

Extraction and presentation

Sodium bis (trimethylsilyl) amide can be obtained by reacting a solution of sodium amide in benzene with hexamethyldisilazane .

${\displaystyle \mathrm {[(CH_{3})_{3}Si]_{2}NH+NaNH_{2}\longrightarrow NaN[Si(CH_{3})_{3}]_{2}+NH_{3}} }$

properties

Sodium bis (trimethylsilyl) amide is a white, hydrolysis-sensitive, crystalline solid that is soluble in many organic solvents . It reacts with water to form sodium hydroxide and hexamethyldisilazane.

use

Sodium bis (trimethylsilyl) amide is used for the production of carbenes , the amination of sulfonamides and the production of lanthanoid complexes. It also serves as a strong base for deprotonation or base-catalyzed reactions, for enolate formation , base for Wittig reactions and, together with alkyllithium, as a superbase component.

Individual evidence

1. ↑ ^{a b c d e f} data sheet Sodium bis (trimethylsilyl) amide, 95% from Sigma-Aldrich , accessed on January 15, 2014 ( PDF ).
2. ↑ Data sheet Sodium bis (trimethylsilyl) amide, 98% from AlfaAesar, accessed on January 15, 2014 ( PDF )(JavaScript required) .
3. ↑ ^{a b} Georg Brauer (Ed.), With the collaboration of Marianne Baudler u a .: Handbook of Preparative Inorganic Chemistry. 3rd, revised edition. Volume I, Ferdinand Enke, Stuttgart 1975, ISBN 3-432-02328-6 , p. 712.
4. ↑ ^{a b} BASF: Sodium Hexamethyldisilazane (NaHMDS) in Tetrahydrofuran  ( page no longer available , search in web archives )  Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. Technical Data Sheet, 2004.