Additional Properties
- Einecs Number 242-169-5
- Synonyms TMSAN
- HMIS 3-3-0-X
- Molecular Formula C5H11NSi
- Molecular Weight (g/mol) 113.23
- Purity (%) 97%
- TSCA No
- Boiling Point (˚C/mmHg) 49-51/10
- Density (g/mL) 0.829
- Flash Point (˚C) 50 °C
- Refractive Index @ 20˚C 1.4204
Application
Review of synthetic utility.1
Following lithiation with LDA may be alkylated with organobromides.2
Cyanomethylates quinolinium methiodides.3
?-lithio derivative reacts with aldehydes to give (Z)-?,?-unsaturated nitriles.4
Used to cyanomethylation of aryl bromides.5
Minireview.6
Under lithium acetate catalysis reacts to cyanomethylate aldehydes and ketones.7
Reference
1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 564-569.
2. Mauze, B. et al. J. Organomet. Chem. 1980, 411, 69.
3. Diaba, F. et al. J. Org. Chem. 2000, 65, 907.
4. Furuta, K. et al. Bull. Chem. Soc. Jpn. 1984, 57, 2768.
5. Wu, L.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 15824.
6. Merino-Montiel, P. Synlett 2009, 507.
7. Kawano, Y. et al. Chem. Lett. 2005, 34, 1508.
Safety
Silane Cross-Coupling Agent
The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.
Trimethylsilylacetonitrile; TMSAN; Cyanomethyltrimethylsilane
Silicon Chemistry, Articles
Silicon-Based Formation of Carbon-Carbon Bonds – Larson
Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products
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