(Trifluoromethyl)trimethylsilane

• Catalog No.: B20347
• CAS Number: 81290-20-2
• M. F.: C4H9F3Si
• M. W.: 142.1949696
• Purity: 98%

SYNONYMS

• Title: (三氟甲基)三甲基硅烷
• IUPAC name: trimethyl(trifluoromethyl)silane
• IUPAC Traditional name: trifluoromethyltrimethylsilane
• Synonyms: Ruppert's Reagent; TFMTMS

DATABASE IDS

• MDL Number: MFCD00145454
• EC Number: 000-000-0
• CAS Number: 81290-20-2
• Beilstein Number: 4241868

PROPERTIES

• Purity: 98%
• Boiling Point: 54-55°C
• Density: 0.962
• Flash Point: -10°C(14°F)
• Refractive Index: 1.3305
• GHS Hazard statements: H225-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-36/37/38
• Safety Statements: 9-16-23-26-33-37
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II

REFERENCES

• Valuable reagent for trifluoromethylation of electrophilic substrates.
• In the presence of F^-, aldehydes and ketones give, after hydrolysis of the intermediate silyl ethers, the trifluoromethyl carbinols: J. Am. Chem. Soc., 111, 393 (1989); J. Org. Chem., 56, 984 (1991); Org. Synth. Coll., 9, 711 (1998):
  
• Alternatively, rapid and efficient trifluoromethylation of carbonyl compounds can be carried out at room temperature in DMSO, in the presence of molecular sieves, without fluoride or other basic catayst: Synlett, 112 (2006). The use of Tri-tert-butylphosphine, 10178 as a catalyst has also been advocated: Synlett, 267 (2006).
• In the presence of CsF and TMS-imidazole, aldimines are converted to ɑ-trifluoromethyl amines: Tetrahedron Lett., 40, 5475 (1999).
• With a catalytic amount of TBAF, excellent yields of trifluoromethyl ketones can be obtained from methyl esters: Angew. Chem. Int. Ed., 37, 820 (1998).
• Similarly, alkyl or aryl thiocyanates are converted to the corresponding trifluoromethyl sulfides in generally good yields: Tetrahedron Lett., 38, 65 (1997). Selenocyanates behave similarly. Trifluoromethylation of aromatics bearing electron-withdrawing groups can be effected in the presence of KF, by displacement of nitro-, cyano- or chloro-substituents: J. Chem. Soc., Perkin 1, 3081 (1998).
• For reviews of this and similar reagents, see: Chem. Rev., 97, 757 (1997); J. Fluorine Chem., 112, 123 (2001).