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Potassium bis(trimethylsilyl)amide

CAS No.
40949-94-8
Chemical Name:
Potassium bis(trimethylsilyl)amide
Synonyms
KHMDS;POTASSIUM HEXAMETHYLDISILAZIDE;HEXAMETHYLDISILAZANE POTASSIUM SALT;HMDS K;KHMDS 0.7M;PotassiumHMDS;Potassium bis(trimet;Potassium bis(trimethyL;potassiumhexamethyldisil;POTASSIUM HEXAMETHYLDISLAZANE
CBNumber:
CB8139300
Molecular Formula:
C6H18KNSi2
Molecular Weight:
199.48
MDL Number:
MFCD00010330
MOL File:
40949-94-8.mol
MSDS File:
SDS
Last updated:2024-04-08 17:36:13

Potassium bis(trimethylsilyl)amide Properties

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
Flash point 45 °F
storage temp. Refrigerator
solubility Miscible with terahydrofuran, ether, benzene and toluene.
form Liquid
Specific Gravity 0.877
color clear to slightly hazy yellow
Water Solubility Reacts with water.
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
Sensitive Moisture Sensitive
BRN 4006754
CAS DataBase Reference 40949-94-8(CAS DataBase Reference)
EPA Substance Registry System Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt (1:1) (40949-94-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
Signal word  Danger
Hazard statements  H314
Precautionary statements  P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes  C,F,Xn
Risk Statements  14-34-67-65-63-48/20-11-40-36/37/38-19-37
Safety Statements  26-36/37/39-45-62-43-46-16-36/37
RIDADR  UN 3263 8/PG 3
WGK Germany  3
1-3-10
TSCA  No
HazardClass  3
PackingGroup  II
HS Code  29319090

Potassium bis(trimethylsilyl)amide price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 277304 Potassium bis(trimethylsilyl)amide solution 0.5 M in toluene 40949-94-8 4x25ml $91.6 2024-03-01 Buy
Sigma-Aldrich 277304 Potassium bis(trimethylsilyl)amide solution 0.5 M in toluene 40949-94-8 2l $880 2024-03-01 Buy
TCI Chemical H0893 Potassium Bis(trimethylsilyl)amide (11% in Toluene, ca. 0.5mol/L) 40949-94-8 100mL $89 2021-12-16 Buy
TCI Chemical H0893 Potassium Bis(trimethylsilyl)amide (11% in Toluene, ca. 0.5mol/L) 40949-94-8 500mL $268 2021-12-16 Buy
Sigma-Aldrich 775061 Potassium bis(trimethylsilyl)amide solution 1.0 M in 2-methyltetrahydrofuran 40949-94-8 4x25ml $327 2024-03-01 Buy
Product number Packaging Price Buy
277304 4x25ml $91.6 Buy
277304 2l $880 Buy
H0893 100mL $89 Buy
H0893 500mL $268 Buy
775061 4x25ml $327 Buy

Potassium bis(trimethylsilyl)amide Chemical Properties,Uses,Production

Chemical Properties

Colorless to amber solution

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.

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

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

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".

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.

Potassium bis(trimethylsilyl)amide Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 279)Suppliers
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View Lastest Price from Potassium bis(trimethylsilyl)amide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
potassium bis(trimethylsilyl)amide pictures 2024-10-15 potassium bis(trimethylsilyl)amide
40949-94-8
US $0.00-0.00 / Kg 1Kg 99.9% 200tons airuikechemical co., ltd.
Potassium bis(trimethylsilyl)amide pictures 2021-07-02 Potassium bis(trimethylsilyl)amide
40949-94-8
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Potassium hexamethyldisilazide pictures 2019-07-10 Potassium hexamethyldisilazide
40949-94-8
US $1.00 / KG 1KG 99% 25kg Career Henan Chemical Co
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