To search by structure, left click in the box below to display the chemdraw toolbar. Then, draw the chemical structure of interest in the box using the toolbar. When your structure is complete, click “Search by Name” or “Search by SMILES” to generate the product name or SMILES respectively. This feature will search within the Gelest product database for matching chemical names or SMILES. Note: In cases where Gelest uses alternate chemical names, it may be necessary to search for the product of interest by its CAS#.
All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.
Alternative Name: RUPPERT'S REAGENT
Specific Gravity: 0.9626
Flashpoint: -10°C (14°F)
HMIS Key: 3-4-0-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.3304
Application: Key reviews.1,2,3
Silylates cyclopropenes to give cyclopropenyltrimethylsilanes.10
Trifluoromethylates terminal acetylenes.11
Gives trifluoromethylthiolation of terminal alkynes in the presence of sulfur.12
Trifluoromethylates carbonyl compounds.4
Converts esters to trifluoromethyl ketones.5
Used to prepare trifluoromethyl vicinal ethylene diamines.6
Used in a simple preparation of potassium (trifluoromethyl)trifluoroborate.7
Used to prepare trifluoromethyltitanium complexes.8
Trifluoromethylates aldehydes, ketones and imines in good yield.9
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. 539-546.
10. Fordyce, E. A. F. et al. J. Chem. Soc., Chem. Commun. 2008, 1124.
11. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262.
12. Chen, C. et al. J. Am. Chem. Soc. 2012, 134, 12454.
2. Prakash, G. et al. Chem. Rev. 1997, 97, 757.
3. Singh, R. P.; Shreeve. J. M. Tetrahedron 2000, 56, 7613.
4. Prakash, G. et al. J. Am. Chem. Soc. 1989, 111, 393.
5. Singh, R. et al. J. Org. Chem. 1999, 64, 2873.
6. Prakash, G. K. S.; Mandal, M. J. Am. Chem. Soc. 2002, 124, 6538.
7. Molander, G. A.; Hoag, B. P. Organometallics 2003, 22, 3313.
8. Taw, F. L. et al. J. Am. Chem. Soc. 2003, 125, 14712.
9. Matsukawa, S.; Saijo, M. Tetrahedron Lett. 2008, 49, 4655.