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Merck
CN

335452

Lithium (trimethylsilyl)acetylide solution

0.5 M in THF

Synonym(s):

(Trimethylsilyl)ethynyllithium

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About This Item

Linear Formula:
(CH3)3SiC≡CLi
CAS Number:
Molecular Weight:
104.15
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3587411
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Product Name

Lithium (trimethylsilyl)acetylide solution, 0.5 M in THF

InChI

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

SMILES string

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

InChI key

ZVXXEONXFWSCIZ-UHFFFAOYSA-N

form

liquid

concentration

0.5 M in THF

density

0.88 g/mL at 25 °C

Quality Level

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Application

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.

Reacts with halotriazines to produce conductive, anisotropic carbon-nitrogen materials.

Packaging

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

wgk

WGK 3

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

flash_point_f

-9.4 °F - closed cup

flash_point_c

-23 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Lithium (Trimethylsilyl) acetylide
Fuhry MM
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
Chemistry of Materials, 6, 636-636 (1994)

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