Potassium bis(trimethylsilyl)amide

Base Information

• Chemical Name: Potassium bis(trimethylsilyl)amide
• CAS No.: 40949-94-8
• Deprecated CAS: 114089-96-2,1637383-71-1,1221402-19-2
• Molecular Formula: C6H19KNSi2
• Molecular Weight: 199.485
• Hs Code.: 29319090
• European Community (EC) Number: 424-100-2,609-880-6
• DSSTox Substance ID: DTXSID00390655
• Nikkaji Number: J409.287B
• Wikipedia: Potassium_bis(trimethylsilyl)amide
• Wikidata: Q903636
• Mol file: 40949-94-8.mol

Synonyms:Potassium bis(trimethylsilyl)amide;40949-94-8;KHMDS;Potassium Hexamethyldisilazide;Hexamethyldisilazane potassium salt;potassium;bis(trimethylsilyl)azanide;Potassium hexamethyldisilyl azide;Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt (1:1);MFCD00010330;potassium bis-trimethylsilylamide;potassium bis-(trimethylsilyl)amide;Potassium Bis(trimethylsilyl)azanide;potassiumbis(trimethylsilyl)amide;Hexamethyldislazane Potassium Salt;potassiumhexamethyldisilazide;potasium hexamethyldisilazide;potassium hexamethyldislazane;SCHEMBL2038;potassium hexamethyidisilazide;potassium hexamethyl disilazide;potassium hexamethyl-disilazide;potassium bistrimethylsilylamide;potassium hexamethyldisilazanide;potassium bistrimethylsilyl amide;potassium bis(trimethylsily)amide;potassium bis(trimethysilyl)amide;DTXSID00390655;IUBQJLUDMLPAGT-UHFFFAOYSA-N;potassium bis(trimethylsily) amide;potassium di-(trimethylsilyl)amide;[bis(trimethylsilyl)amino]potassium;potassium bis (trimethylsilyl)amide;potassium bis(trimethylsilyl) amide;potassium bis(trimethylsilyl)-amide;Potassium bis (trimethylsilyl) amide;potassium bis-(trimethylsilyl)-amide;AKOS015909125;potassium N,N-bis(trimethylsilyl)amide;s13925;Potassium bis(trimethylsilyl)amide, 95%;BP-12745;BP-21018;Potassium hexamethyldisilazane 20% in THF;Potassium hexamethyldisilazane, 1M in THF;FT-0605922;H0893;P2730;potassium 1,1,1,3,3,3-hexamethyl-disilazane;1,1,1,3,3,3-hexamethyldisilazane potassium salt;A825360;Potassium bis(trimethylsilyl)amide 11% in toluene;Q903636;Potassium bis(trimethylsilyl)amide, 15 wt. % in toluene;Potassium Bis(trimethylsilyl)amide (14% in Toluene, ca. 0.6mol/L);3-(5-(Pyridin-4-ylmethyl)-5H-cyclopenta[1,2-b:5,4-b']dipyridin-5-yl)cyclohexanone

Chemical Property of Potassium bis(trimethylsilyl)amide

Chemical Property:

• Appearance/Colour: Colorless to amber solution
• Vapor Pressure: 54 mm Hg ( 25 °C)
• Melting Point: 194-195°C
• Refractive Index: 1.4920
• Boiling Point: 126 °C at 760 mmHg
• Flash Point: 30 °C
• PSA: 3.24000
• Density: 0.877 g/cm³
• LogP: 2.42250
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with terahydrofuran, ether, benzene and toluene.
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 199.06148413
• Heavy Atom Count: 10
• Complexity: 80.9

Purity/Quality:

99% ^*data from raw suppliers

PotassiumBis(trimethylsilyl)amide(0.5MTolueneSolution) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, F
• Hazard Codes: C,F,Xn
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)[N-][Si](C)(C)C.[K+]
• General Description: Potassium bis(trimethylsilyl)amide (KHMDS) is a strong, non-reversible base commonly used in synthetic chemistry to facilitate deprotonation reactions under mild conditions. It is particularly valuable in transition-metal-free protocols, such as cross-dehydrogenative coupling (CDC), where it enables reactions at lower temperatures (e.g., room temperature) compared to traditional methods. Additionally, KHMDS serves as a key reagent in the synthesis of lanthanide complexes, where it reacts with lanthanide triiodides to form heteroleptic bis(trimethylsilyl)amide compounds, which can be further characterized and utilized as precursors for catalytic applications. Its versatility and strong basicity make it a widely employed reagent in organic and inorganic synthesis.

Technology Process of Potassium bis(trimethylsilyl)amide

There total 6 articles about Potassium bis(trimethylsilyl)amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

lithium bis(trimethylsilyl)amide diethyl etherate (18400-61-8) → potassium hexamethylsilazane (40949-94-8)

Guidance literature:

With potassium tert-butylate; In benzene; at 20 ℃;

DOI:10.1021/acs.organomet.6b00256

Reference yield:

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → potassium hexamethylsilazane (40949-94-8)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 3.25h; Irradiation;

DOI:10.1080/00397919508011786

Reference yield:

tetrakis(trimethylsilyl)tetrazene (52764-24-6) → potassium hexamethylsilazane (40949-94-8)

Guidance literature:

With potassium; In diethyl ether; at 25 ℃; for 1h;

upstream raw materials:

tetrakis(trimethylsilyl)tetrazene

1,1,1,3,3,3-hexamethyl-disilazane

hexamethyldisilazan

lithium bis(trimethylsilyl)amide diethyl etherate

Downstream raw materials:

1,1,1,3,3,3-hexamethyl-disilazane

N'-isopropyl-1,1-dimethyl-N,N-bis(trimethylsilyl)silanediamine

2,4-diisopropyl-1,1,3,3-tetramethylcyclodisilazane

Potassium; 2,3,4-trimethyl-naphthalen-1-olate

Refernces

Low-Temperature, Transition-Metal-Free Cross-Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles

10.1021/acs.joc.7b02085

This research presents a low-temperature, transition metal-free cross dehydrogenative coupling (CDC) protocol for the synthesis of 3,3-disubstituted oxindoles, which are important heterocyclic compounds with significant biological properties and potential applications in medicinal chemistry. The study aims to address the high reaction temperatures typically required for such syntheses, which can limit substrate scope and preclude thermally-sensitive substrates and products. The new procedure utilizes a strong, non-reversible base to significantly lower the reaction temperature to room temperature, resulting in a safer and more accessible method. Key chemicals used in the process include KHMDS as the base, iodine as the oxidant, and various anilides as substrates.

Iodo bis bistrimethylsilylamido lanthanides

10.1016/S0022-328X(01)00793-8

The research primarily focuses on the synthesis and characterization of heteroleptic iodo bis(trimethylsilyl)amide complexes of lanthanum, samarium, and ytterbium. The reactions were initiated by reacting lanthanide triiodides with potassium bis(trimethylsilyl)amide in THF, leading to the formation of bisamide and trisamide compounds. For lanthanum, recrystallization from THF-toluene yielded monocrystals of the dimeric bisamide [La(μ-I){N(TMS)2}2(THF)]2. The study utilized various analytical techniques including NMR spectroscopy, X-ray crystallography, infrared spectroscopy, and elemental analysis to characterize the synthesized compounds. The research also explored the potential of these complexes as precursors for the preparation of ytterbium-based catalysts for Diels–Alder reactions.