1-Trimethylsilyl-1-hexyne - CAS 3844-94-8

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Category
Main Product
Product Name
1-Trimethylsilyl-1-hexyne
Catalog Number
3844-94-8
Synonyms
1-HEXYN-1-YLTRIMETHYLSILANE; 1-TRIMETHYSILYL-1-HEXYNE; 1-TRIMETHYLSILYL-1-HEXYNE; TIMTEC-BB SBB009058; 1-Trimethyl; (1-Hexynyl)trimethylsilane
CAS Number
3844-94-8
Molecular Weight
154.32
Molecular Formula
C9H18Si
COA
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MSDS
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Canonical SMILES
CCCCC#C[Si](C)(C)C
InChI
InChI=1S/C9H18Si/c1-5-6-7-8-9-10(2,3)4/h5-7H2,1-4H3
InChIKey
SFCRJYVNDZSYCT-UHFFFAOYSA-N
Structure
CAS 3844-94-8 1-Trimethylsilyl-1-hexyne
Specification
Purity
95%
Boiling Point
65ºC (35 mmHg)
Density
0.764
Related Products
Reference Reading
1.Tetrabutylammonium fluoride (TBAF)-catalyzed addition of substituted trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones.
Chintareddy VR1, Wadhwa K, Verkade JG. J Org Chem. 2011 Jun 3;76(11):4482-8. doi: 10.1021/jo200314g. Epub 2011 May 12.
Herein we report that tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF solvent at room temperature. The reaction conditions are mild and operationally simple, and a variety of aryl functional groups, such as chloro, trifluoromethyl, bromo, and fluoro groups, are tolerated. Impressively, using our protocol, useful CF(3)-bearing tertiary propargylic alcohols can be synthesized. Product yields are generally better than or comparable to those in the literature. 1-Phenyl-2-trimethylsilyl acetylene, trimethyl ((4-(trifluoromethyl)phenyl)ethynyl)silane, 1-trimethylsilyl-1-hexyne, and trimethyl(thiophen-3-ylethynyl)silane underwent clean conversion to their corresponding propargylic alcohols as products under our conditions. Heterocyclic carbonyl compounds, such as furan-3-carboxaldehyde, thiophene-3-carboxaldehyde, and 2-pyridyl ketone, gave good yields of propargylic alcohols.
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