Skip to Content
Merck
All Photos(1)

Documents

939048

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide ChemBeads

new

Synonym(s):

Hexamethyldisilazane lithium salt ChemBeads

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
LiC6H18NSi2
Molecular Weight:
167.33
UNSPSC Code:
12352100

description

Organic Salt

Quality Level

100

form

solid

composition

14-16 wt% loading of base

reaction suitability

core: lithium

SMILES string

[Li]N([Si](C)(C)C)[Si](C)(C)C

InChI

1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1

InChI key

YNESATAKKCNGOF-UHFFFAOYSA-N

General description

Lithium bis(trimethylsilyl)amide is a non-nucleophilic strong Brønsted base, which is generally soluble in most of the nonpolar organic solvents. It is most commonly employed in organic reactions.

Application

Base employed in generating enolates for the preparation of lactone precursors, pyranones, and cyclohexanes. Used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines.[6] Also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles. For general uses, product is also available in powdered form (324620)

Features and Benefits

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

Other Notes

related product

Product No.
Description
Pricing

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H228,H251,H314

Hazard Classifications

Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

62.6 °F - closed cup

Flash Point(C)

17 °C - closed cup

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCW2491

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Structural Studies of Cesium, Lithium/Cesium, and Sodium/Cesium Bis(trimethylsilyl)amide (HMDS) Complexes
Ojeda-Amador A I, et al.
Inorganic Chemistry, 55(11), 5719-5728 (2016)
ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand
Aguirre A L, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 27(51), 12981-12986 (2021)
Alkali-metal-catalyzed addition of primary and secondary phosphines to carbodiimides. A general and efficient route to substituted phosphaguanidines
Zhang W X, et al.
Chemical Communications (Cambridge, England), 3812-4, 36-36 (2006)
High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads
Tu N P, et al.
Angewandte Chemie (International Edition in English), 58(24), 7987-7991 (2019)
Ana L Aguirre et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(51), 12981-12986 (2021-07-08)
High-throughput experimentation (HTE) methods are central to modern medicinal chemistry. While many HTE approaches to C-N and Csp2 -Csp2 bonds are available, options for Csp2 -Csp3 bonds are limited. We report here how the adaptation of nickel-catalyzed cross-electrophile coupling of
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service