| Identification | More | [Name]
Potassium bis(trimethylsilyl)amide | [CAS]
40949-94-8 | [Synonyms]
1,1,1,3,3,3-HEXAMETHYLDISILAZANE POTASSIUM SALT
HEXAMETHYLDISILAZANE POTASSIUM SALT
HEXAMETHYLDISLAZANE POTASSIUM SALT
KHMDS
POTASSIUM BIS(TRIMETHYLSILYL)AMIDE
POTASSIUMHEXAMETHYLDISILAZANE
POTASSIUM HEXAMETHYLDISILAZIDE
POTASSIUM HEXAMETHYLDISLAZANE
HexamethyldisilazanePotassiumSalt(15%inToluene)
potassiumhexamethyldisilazane(solutioninthf)
potassiumhexamethyldisilazane,khmds,in
potassiumhexamethyldisilazane,khmds,intetrahydrofuran
potassiumhexamethyldisilazane,khmds,intoluene
KHMDS~Potassium hexamethyldisilazide
Potassium hexamethyldisilazane, in tetrahydrofuran
Potassium hexamethyldisilazane, in toluene
POTASSIUM BIS(TRIMETHYLSILYL)AMIDE SOL., ~0.5 M IN TOLUENE
POTASSIUM BIS(TRIMETHYLSILYL)AMIDE, 0.5M SOLUTION IN TOLUENE
POTASSIUM BIS(TRIMETHYLSILYL)AMIDE, DRY POWDER
PotassiumhexamethyldislazaneinTHF | [EINECS(EC#)]
424-100-2 | [Molecular Formula]
C6H18KNSi2 | [MDL Number]
MFCD00010330 | [Molecular Weight]
199.48 | [MOL File]
40949-94-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to amber solution | [Melting point ]
194-195°C | [Boiling point ]
111 °C | [density ]
0.877 g/mL at 25 °C
| [vapor density ]
3.2 (vs air)
| [vapor pressure ]
54 mm Hg ( 25 °C)
| [refractive index ]
1.4920 | [Fp ]
45 °F
| [storage temp. ]
Refrigerator | [solubility ]
Miscible with terahydrofuran, ether, benzene and toluene. | [form ]
Liquid | [color ]
clear to slightly hazy yellow | [Specific Gravity]
0.877 | [Water Solubility ]
Reacts with water. | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [Detection Methods]
T | [BRN ]
4006754 | [CAS DataBase Reference]
40949-94-8(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt (1:1) (40949-94-8) |
| Safety Data | Back Directory | [Hazard Codes ]
C,F | [Risk Statements ]
R14:Reacts violently with water.
R34:Causes burns.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R63:Possible risk of harm to the unborn child.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S46:If swallowed, seek medical advice immediately and show this container or label .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 3263 8/PG 3
| [WGK Germany ]
3
| [F ]
1-3-10 | [TSCA ]
No | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to amber solution | [Uses]
Potassium Bis(trimethylsilyl)amide (1M in THF) is used in the preparation of 5-azacytidine, an antineoplastic drug. Also applied in the preparation of β3-AR agonists used in anti-stress formulations. It is also used as a reagent in the preparation of lanthanide complexes employed in selective cyclization reactions. | [Uses]
Potassium bis(trimethylsilyl)amide is a strong base used in the alkylation carbonyl compounds.1
| [Uses]
Potassium Hexamethyldisilazide is widely used as a Sterically Hindered Base for Enolate Generation in Selective Formation of Linear Conjugated Dienolates and Alkyl (Z)-3-Alkenoates. | [Preparation]
Potassium Hexamethyldisilazide is prepared and isolated by the procedure
of Wannagat and Niederpruem. A more convenient in situ
generation from potassium hydride and hexamethyldisilane is
described by Brown. | [General Description]
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product, 1.0 M in 2-methyltetrahydrofuran aligns with "Safer Solvents and Auxiliaries", "Use of Renewable Feedstocks" and "Inherently Safer Chemistry for Accident Prevention". Click here for more information. | [Synthesis]
Potassium bis(trimethylsilyl)amide is an important non-nucleophilic base widely used in organic synthesis. The main method for its preparation is are interaction of hexamethyldisilazane with potassium amide) potassium hydride, potassium metal, mad styrene, isoprene, or naphthalene as electron acceptors.
An oven-dried 100 ml round-bottom flask was charged with KH (3.22 g, 20.1 mmol, 25 wt. 96 in oil) and flushed with argon. The hydride was then washed with hexane (4x5 ml). To the flask was fitted, a reflux condenser was made, and then THF (20 ml) and bis(trimethylsi1yl)amine (3.81 ml, 18.1 mmol) were added. The resultant slurry was sonicated until the hydrogen gas evolution had ceased, and almost all the potassium hydride had been consumed (3.25 h). The slurry was allowed to settle, and the supernatant was then cannulated into a Schlenk flask. Titration4 for the amide base concentration showed it to be 0.80 M, while the concentration of the total base was 0.86 M[1-2].
| [References]
[1] I. V. Magedov. “Convenient method for the preparation of a solution of potassium bis(trimethylsilyl)amide.” Russian Chemical Bulletin 44 11 (1995): 2197–2198.
[2] J. Ahman, P. Somfai. “An Efficient Preparation of Potassium Bis (Trimethylsilyl) Amide (KHMDS).” Synthetic Communications 25 1 (1995): 2301–2303.
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