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TRIMETHYLSILYLACETONITRILE
Boiling Point: 49-51° / 10
EINECS Number: 242-169-5
Molecular Weight: 113.23
Alternative Name: TMSAN
Specific Gravity: 0.829
Flashpoint: 50°C (122°F)
HMIS Key: 3-3-0-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Formula: C5H11NSi
Refractive Index: 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.
Fieser:
Silanes
Silicon-Based Cross-Coupling Reagents
Enabling Synthetic Organic Transformations
Silicon-Based Formation of Carbon-Carbon Bonds – Larson