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Lithium bis(trimethylsilyl)amide

Lithium bis(trimethylsilyl)amide Basic information
Product Name:Lithium bis(trimethylsilyl)amide
Synonyms:HEXAMETHYLDISILAZANE LITHIUM SALT;LITHIUM-BIS-(TRIMETHYLSILYL)-AMID;LITHIUM BIS(TRIMETHYLSILYL)AMIDE;Lithium bis(trimethylsilyl)amide, 0.9-1.1M in hexane, packaged under Argon in resealable ChemSeal bottles;Lithium bis(trimethylsilyl)amide, 1.0m solution in methyl tert-butyl ether;Lithium bis(trimethylsilyl)amide1.0M sol. in methyl tert-butyl etherAcroSeal§3;Lithium bis(trimethylsilyl)amide1M solution in THF/EthylbenzeneAcroSeal§3;Lithium bis(trimethylsilyl)amide0.9M solution in methylcyclohexaneAcroSeal§3
CAS:4039-32-1
MF:C6H18LiNSi2
MW:167.33
EINECS:223-725-6
Product Categories:Classes of Metal Compounds;Li (Lithium) Compounds;Si (Classes of Silicon Compounds);Silazanes;Silicon Compounds (for Synthesis);Si-N Compounds;Synthetic Organic Chemistry;Typical Metal Compounds
Mol File:4039-32-1.mol
Lithium bis(trimethylsilyl)amide Structure
Lithium bis(trimethylsilyl)amide Chemical Properties
Melting point 73°C
Boiling point 55-56 °C
density 0.860 g/mL at 25 °C (lit.)
refractive index n20/D 1.425(lit.)
Fp 48 °F
storage temp. Store below +30°C.
solubility hydrolysis
form Powder
color White
Specific Gravity0.716
Water Solubility hydrolysis
Sensitive Air & Moisture Sensitive
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
BRN 3567910
Exposure limitsACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
InChIKeyYNESATAKKCNGOF-UHFFFAOYSA-N
CAS DataBase Reference4039-32-1(CAS DataBase Reference)
EPA Substance Registry SystemSilanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, lithium salt (4039-32-1)
Safety Information
Hazard Codes F,C,N
Risk Statements 11-34-48/20-63-65-67-51/53-35-20-62-14-40-37-19
Safety Statements 9-16-26-29-33-36/37/39-45-61-62-57-43
RIDADR UN 2925 4.1/PG 2
WGK Germany 3
F 10-23
TSCA Yes
HazardClass 4.3
PackingGroup II
HS Code 29319090
MSDS Information
ProviderLanguage
Lithium hexamethyldisilazide English
SigmaAldrich English
ACROS English
ALFA English
Lithium bis(trimethylsilyl)amide Usage And Synthesis
Chemical Propertieslight yellow to yellow crystalline powder
Physical propertiesdistillable low-melting solid; mp 70–72 °C, bp 115 °C/1mmHg. LHMDS is a cyclic trimer in the solid state,3 whereas in benzene solution it exists in a monomer–dimer equilibrium. LHMDS exists as a tetramer-dimer mixture in hydrocarbons and as a dimer-monomer mixture in THF and ether. Treatment of LHMDS with trialkylamines increases the monomer concentration, whereas the use of diamines affords exclusively the corresponding chelated monomer. LHMDS is less soluble, less basic, more stable, and much less sensitive to air compared to lithium diisopropylamide. pKa 29.5 (THF, 27 °C).
UsesLithium Hexamethyldisilazide is widely used as strong nonnucleophilic base
UsesLithium bis(trimethylsilyl)amide is a base used in preparation of dienes and enolates. It is used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines. Lithium bis(trimethylsilyl)amide is also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles.
UsesLithium bis(trimethylsilyl)amide is used as nonnucleophilic base to generate kinetic ketone and ester enolates. It is considerably more selective than LDA and undesired reductions (e.g., of nonenolizable ketones observed in the case of LDA) can be avoided by using LHMDS.
PreparationIt is conveniently prepared by the reaction of hexamethyldisilazane with n-butyllithium in hexane. For most uses the hexane is then evaporated and replaced with THF.
General DescriptionThis product, 0.5 M in 2-methyltetrahydrofuran aligns with Safer Solvents and Auxiliaries, Use of Renewable Feedstocks and Inherently Safer Chemistry for Accident Prevention.
Flammability and ExplosibilityHighlyflammable
Lithium bis(trifluoromethanesulphonyl)imide Methanesiliconic acid sodium salt RINK AMIDE RESIN Lithium silicon tert-Butyl methyl ether 4-[(2,4-Dimethoxyphenyl)(Fmoc-amino)methyl]phenoxyacetic acid Trimethylsilylacetylene Release agent No.8 Lithium amide Tetrahydrofuran Lithium oxide Methyllithium Lithium hydride N-(Trimethylsilyl)acetamide 1,1,3,3-TETRAMETHYLDISILAZANE Silicone rubber,methyl-vinyl Fomesafen Lithium Lihmds 1m In Thf
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