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Product Code: SIT8384.0

Cas No: 13154-24-0

R&D quantities:

100 g
25 g
750 g

Interested in a Commercial Order?

Boiling Point: 79-80° / 10

Molecular Weight: 192.81

Alternative Name: TIPS-CHLORIDE

Specific Gravity: 0.903

Flashpoint: 62°C (144°F)

HMIS Key: 3-2-1-X

Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

Formula: C9H21ClSi

Refractive Index: 1.4520

Application: Review of synthetic utility.1
Review on organosilane protecting groups.2
Employed in nucleotide synthesis.3
Protection and stereocontrol of reaction of pyrroles.4
Quantitatively converts O-acetyl-protected glycosylthiomethyl phosphonate esters to their phosphonates.5
Used to form stable enol silyl ethers that can be oxidized to enones or ?-TIPS-enones.6
Reacts with hydrazine to form the mono-TIPShydrazine, which can be converted to TIPS-protected hydrazones and further to unsymmetrical azines.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. 554-558.
2. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
3. Ogilvie, K. et al. Tetrahedron Lett. 1974, 2861. Ogilvie, K. et al. Carbohyd., Nucleosides, Nucleotides 1976, 3, 197.
4. Pattenden, G.; Robertson, G. M. Tetrahedron Lett. 1986, 27, 399.
5. Zhu, X. et al. J. Org. Chem. 2004, 69, 6843.
6. Yu, J.-Q. et al. Org. Lett. 2005, 7, 1415.
7. Justo de Pomar, J. C.; Soderquist, J. A. Tetrahedron Lett. 2000, 41, 3285.

Fieser: F&F: Vol. 5, p 75.

Additional Properties: 255