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Potassium bis(trimethylsilyl)amide

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Potassium bis(trimethylsilyl)amide Basic information

Product Name:
Potassium bis(trimethylsilyl)amide
Synonyms:
  • 1,1,1,3,3,3-HEXAMETHYLDISILAZANE POTASSIUM SALT
  • KHMDS
  • HEXAMETHYLDISILAZANE POTASSIUM SALT
  • HEXAMETHYLDISLAZANE POTASSIUM SALT
  • POTASSIUM BIS(TRIMETHYLSILYL)AMIDE
  • POTASSIUMHEXAMETHYLDISILAZANE
  • POTASSIUM HEXAMETHYLDISILAZIDE
  • POTASSIUM HEXAMETHYLDISLAZANE
CAS:
40949-94-8
MF:
C6H18KNSi2
MW:
199.48
EINECS:
424-100-2
Product Categories:
  • 25mL Sure/Seal Reagents
  • Aliphatics
  • Chemical Synthesis
  • Organic Bases
  • Organometallic Reagents
  • Synthetic Reagents
  • Analytical Chemistry
  • GC Derivatizing Reagents
  • Si (Classes of Silicon Compounds)
  • Classes of Metal Compounds
  • K (Potassium) Compounds (excluding simple potassium salts)
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Typical Metal Compounds
  • Silazanes
  • Silylation (GC Derivatizing Reagents)
  • Si-N Compounds
  • Trimethylsilylation (GC Derivatizing Reagents)
Mol File:
40949-94-8.mol
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Potassium bis(trimethylsilyl)amide Chemical 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)
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Safety Information

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

MSDS

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Potassium bis(trimethylsilyl)amide Usage And Synthesis

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".

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