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Boiling Point: 55°
Molecular Weight: 142.20
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.