lithium(1+) ion bis(trimethylsilyl)azanide

• ChemBase ID: 128076
• Molecular Formular: C6H18LiNSi2
• Molecular Mass: 167.32582
• Monoisotopic Mass: 167.1137822
• SMILES: C[Si](C)(C)[N-][Si](C)(C)C.[Li+]
• Canonical SMILES: C[Si]([N-][Si](C)(C)C)(C)C.[Li+]
• InChI: InChI=1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
• InChIKey: YNESATAKKCNGOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion bis(trimethylsilyl)azanide
• IUPAC Traditional name: lithium(1+) ion bis(trimethylsilyl)azanide
• Synonyms: Lithium bis(trimethylsilyl)amide and lithium hexamethyldisilazide; Lithium bis(trimethylsilyl)amide; LHMDS; Lithium hexamethyldisilazide; Lithium bis(trimethylsilyl)amide; Lithium bis(trimethylsilyl)amide, 0.9-1.1M in hexane; 双(三甲基硅基)氨基锂; 双(三甲基硅基)氨基锂, 0.9-1.1M 正己烷溶液, 氩气下可重封的ChemSeal™瓶包装

Database IDs

• CAS Number: 4039-32-1
• EC Number: 223-725-6
• MDL Number: MFCD00008261
• PubChem SID: 162222392
• PubChem CID: 2733832
• Wikipedia Title: Lithium_bis(trimethylsilyl)amide

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.8950769
• LogD (pH = 7.4): -0.8299159
• Log P: 2.7111
• Molar Refractivity: 39.3948 cm^3
• Polarizability: 18.492445 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: decomposes in water; THF, hexane
• Apperance: Liquid; Powder, Packaged under argon; White solid
• Melting Point: 71-72 °C; 83-86°C
• Boiling Point: 80 - 84 °C (0.001 mm Hg)
• Flash Point: -17°C(1°F); -31°C(-24°F)
• Density: 0.716; 0.891

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N); X
• UN Number: UN2924; UN3396
• Hazard Class: 3; 4.3
• Packing Group: II
• Risk Statements: 11-14/15-34; 11-14-19-34; 11-14-34-48/20-62-51/53-67
• Safety Statements: 16-26-36/37/39-43-45; 16-26-36/37/39-43-45-57; 8-16-26-36/37/39-43-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08; GHS09
• Main Hazard: flammable
• GHS Hazard statements: H225-H304-H361-H373-H314-H336-H411; H225-H314-H318; H261-H228-H314-H318
• GHS Precautionary statements: P210-P280-P305+P351+P338-P309-P310-P402; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A

Product Information

• Purity: 20% (ca 1.06M) soln. in THF/ethylbenzene
• Concentration: 0.9-1.1M in hexane
• Packaging: packaged in resealable septum cap bottle; packaged under Argon in resealable ChemSeal? bottles

REFERENCES

• Versatile non-nucleophilic strong base. For examples of use in the lithiation of ethyl acetate, see: Org. Synth. Coll., 6, 598 (1988), and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones: Org. Synth. Coll., 9, 442 (1998).
• Supplied in septum cap bottle.