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335452

Sigma-Aldrich

Lithium (trimethylsilyl)acetylide solution

0.5 M in THF

Synonym(s):
(Trimethylsilyl)ethynyllithium
Linear Formula:
(CH3)3SiC≡CLi
CAS Number:
Molecular Weight:
104.15
Beilstein:
3587411
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

concentration

0.5 M in THF

density

0.88 g/mL at 25 °C

SMILES string

[Li]C#C[Si](C)(C)C

InChI

1S/C5H9Si.Li/c1-5-6(2,3)4;/h2-4H3;

InChI key

ZVXXEONXFWSCIZ-UHFFFAOYSA-N

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Application

Reacts with halotriazines to produce conductive, anisotropic carbon-nitrogen materials.
Lithium (trimethylsilyl)acetylide can be used as a reagent:
  • In the transmetalation and nucleophilic displacement reactions.
  • To prepare propargylic alcohol derivatives by reacting with aldehydes and ketones.
  • To synthesize α,βynones by treating with Weinreb amide or with isoxazolidide.
  • Along with Grignard reagent to convert γ- and δ-thiolactams to thioiminium salts, which are employed as key intermediates to produce disubstituted pyrrolidines.

Packaging

4×25, 50, 500 mL in Sure/Seal™
The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-9.4 °F - closed cup

Flash Point(C)

-23 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Chemistry of Materials, 6, 636-636 (1994)
Sequential addition reaction of lithium acetylides and Grignard reagents to thioiminium salts from thiolactams leading to 2, 2-disubstituted cyclic amines
M Toshiaki, et al.
Tetrahedron, 62(26), 6312-6320 (2006)
Lithium (Trimethylsilyl) acetylide
Fuhry MM
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

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