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939048

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide ChemBeads

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Synonym(s):

Hexamethyldisilazane lithium salt ChemBeads

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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

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Product No.
Description
Pricing

pictograms

FlameCorrosion
GHS02,GHS05

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Danger

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

62.6 °F - closed cup

flash_point_c

17 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW2491

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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)
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)
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)
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
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