939048
Lithium bis(trimethylsilyl)amide ChemBeads
solid
Synonym(s):
Hexamethyldisilazane lithium salt ChemBeads
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About This Item
Empirical Formula (Hill Notation):
LiC6H18NSi2
Molecular Weight:
167.33
MDL number:
UNSPSC Code:
12352100
Product Name
Lithium bis(trimethylsilyl)amide ChemBeads,
description
Organic Salt
Quality Level
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
- High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads
- Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughout Experimentation
- ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B
Supplementary Hazards
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
Regulatory Information
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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)
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)
Tatsuya Nitabaru et al.
Journal of the American Chemical Society, 131(38), 13860-13869 (2009-09-10)
Full details of an anti-selective catalytic asymmetric nitroaldol reaction promoted by a heterobimetallic catalyst comprised of Nd(5)O(O(i)Pr)(13), an amide-based ligand, and NaHMDS (sodium hexamethyldisilazide) are described. A systematic synthesis and evaluation of amide-based ligands led to the identification of optimum
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