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
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
Related Categories
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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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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