potassium bis(trimethylsilyl)azanide

• ChemBase ID: 287468
• Molecular Formular: C6H18KNSi2
• Molecular Mass: 199.48312
• Monoisotopic Mass: 199.06148433
• SMILES: C[Si]([N-][Si](C)(C)C)(C)C.[K+]
• Canonical SMILES: C[Si]([N-][Si](C)(C)C)(C)C.[K+]
• InChI: InChI=1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
• InChIKey: IUBQJLUDMLPAGT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium bis(trimethylsilyl)azanide
• IUPAC Traditional name: potassium bis(trimethylsilyl)azanide
• Synonyms: Potassium bis(trimethylsilyl)amide; KHMDS; Potassium hexamethyldisilazide; Potassium bis(trimethylsilyl)amide; 双(三甲基硅基)氨钾; 双(三甲基硅基)氨基钾

Database IDs

• CAS Number: 40949-94-8
• EC Number: 424-100-2
• MDL Number: MFCD00010330
• Beilstein Number: 4006754
• PubChem SID: 180672999
• PubChem CID: 3251421

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

• Apperance: Liquid
• Boiling Point: 66°C
• Flash Point: -14°C(6°F); 7°C(44°F)
• Density: 0.881; 0.910
• Refractive Index: 1.4900; 1.4920

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: UN2924
• Hazard Class: 3
• Packing Group: II
• Risk Statements: 11-14-19-34; 11-14-19-34-37; 11-14-34-48/20-63-67
• Safety Statements: 8-16-26-36/37/39-45; 8-16-26-36/37/39-46; 8-9-16-20-23-26-30-33-36/37/39-45-60
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Hazard statements: H225-H314-H318; H225-H314-H318-H361-H373-H336; H225-H314-H351-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P301+P310-P305+P351+P338-P315-P402; P210-P280-P305+P351+P338-P309-P310-P402

Product Information

• Purity: 15% w/w in toluene; 20% w/w, 0.91M in THF; 95+%
• Concentration: 20% w/w, 0.91M in THF
• Packaging: packaged under Argon in resealable ChemSeal? bottles

REFERENCES

• Sterically hindered strong base, compare Sodium bis(trimethylsilyl)amide, L13352 and Lithium bis(trimethylsilyl)amide, L15012. Used in the generation of K enolates, preferred to their Li or Na counterparts in some reactions, see e.g.: Tetrahedron Lett., 32, 1779 (1991); J. Am. Chem. Soc., 109, 6881 (1987); 111, 1063 (1989).
• Also used in the Wittig reaction, to give Li salt-free product distribution for selective (Z)-alkene formation: J. Org. Chem., 45, 4260 (1980). Has also been used with 18-crown-6 for selective formation of (Z)-ɑ?-unsaturated esters from phosphonates: Tetrahedron Lett., 24, 4405 (1983).