Molecular structure of (Trimethylsilyl)acetonitrile, CAS Number: 18293-53-3
(Trimethylsilyl)acetonitrile (CAS 18293-53-3)
Alternate Names:
(Cyanomethyl)trimethylsilane
CAS Number:
18293-53-3
Purity:
≥95%
Molecular Weight:
113.23
Molecular Formula:
C5H11NSi
Supplemental Information:
This is as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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(Trimethylsilyl)acetonitrile, also known as TMSA, is an organic compound with a wide range of applications. Particularly in biochemistry and physiology, it can be used to selectively label proteins and nucleic acids. It is also a reagent in the synthesis of several organic compounds, such as ketones, alcohols, and amines. (Trimethylsilyl)acetonitrile finds applications in polymer synthesis and serves as a catalyst in various reactions. It has inhibited both acetylcholinesterase, which is involved in the regulation of neurotransmitter release, and cyclooxygenase-2, an enzyme linked to inflammation.
(Trimethylsilyl)acetonitrile (CAS 18293-53-3) References
- Cyclization reactions of dianions in organic synthesis. | Langer, P. and Freiberg, W. 2004. Chem Rev. 104: 4125-50. PMID: 15352788
- Mild palladium-catalyzed selective monoarylation of nitriles. | Wu, L. and Hartwig, JF. 2005. J Am Chem Soc. 127: 15824-32. PMID: 16277525
- Synthesis of (+)-complanadine A, an inducer of neurotrophic factor excretion. | Yuan, C., et al. 2010. J Am Chem Soc. 132: 5924-5. PMID: 20387896
- An efficient aldol-type direct reaction of isatins with TMSCH2CN. | Bhaskara Rao, VU., et al. 2015. Org Biomol Chem. 13: 9755-9. PMID: 26347285
- Fluoride-ion mediated reaction between trimethylsilylacetonitrile and carbonyl compounds. A new synthesis of β-trimethylsilyloxy nitrites. Journal of the Chemical Society | Palomo, C., Aizpurua, J. M., López, M. C., & Lecea, B. 1989. Perkin Transactions 1. (9): 1692-1694.
- Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl) acetonitrile | Kawano, Y., Kaneko, N., & Mukaiyama, T. 2005. Chemistry letters. 34(11): 1508-1509.
- Stereocontrolled synthesis of (5+ 5),(5+ 6) and (6+ 6) 3-spiropseudonucleosides | Gasch, C., Illangua, J. M., Merino-Montiel, P., & Fuentes, J. 2009. Tetrahedron. 65(21): 4149-4155.
- Chemoenzymatic method for the preparation of γ-amino alcohols from phenylfuran-based aldehydes; lipase-catalyzed kinetic resolution of β-hydroxy nitriles | Turcu, M. C., Perkiö, P., & Kanerva, L. T. 2010. Tetrahedron: Asymmetry. 21(6): 739-745.
- Stereoselective synthesis of piperidinone and quinolinone systems via ring opening reactions using TiCl4/silyl reagents | Muthusamy, S., Gangadurai, C., Krishnamurthi, J., & Suresh, E. 2011. Tetrahedron. 67(23): 4212-4220.
- Palladium-catalyzed carbonylation with Mo (CO) 6 for the synthesis of benzoylacetonitriles | Pyo, A., Park, A., Jung, H. M., & Lee, S. 2012. Synthesis. 44(18): 2885-2888.
- One-pot synthesis of benzoylacetonitriles through sequential Pd-catalyzed carbonylation and decarboxylation | Lee, S., Kim, H. S., Min, H., & Pyo, A. 2016. Tetrahedron Letters. 57(2): 239-242.
- Mukaiyama addition of (trimethylsilyl) acetonitrile to dimethyl acetals mediated by trimethylsilyl trifluoromethanesulfonate | Downey, C. W., Lee, A. Y. K., Goodin, J. R., Botelho, C. J., & Stith, W. M. 2017. Tetrahedron Letters. 58(36): 3496-3499.
- Pyridinic nitrogen-rich carbon nanocapsules from a bioinspired polydopamine derivative for highly efficient electrocatalytic oxygen reduction | Yi, Z., Zhang, Z., Wang, S., & Shi, G. 2017. Journal of Materials Chemistry A. 5(2): 519-523.
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
(Trimethylsilyl)acetonitrile, 5 g | sc-251367 | 5 g | $490.00 |