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TFA

(Trifluoroacetic Acid)


Other Names:

2,2,2-Trifluoroethanoic acid

Trifluoroethanoic acid





General Information:


Structure:



CAS Number: 76-05-1

Molecular Weight: 114.02 g/mol

Appearance: Colorless liquid


Trifluoroacetic acid (TFA) is a strong organic acid typically used as a solvent or acid catalyst. TFA is the CF3 analogue of acetic acid (AcOH) which due to the electron withdrawing effect of the fluorine atoms is much more acidic than AcOH. The pKa of TFA is 0.23, compared to a pKa of 4.76 for AcOH. The low boiling point (bp = 72 C) of TFA facilitates simpler product isolation due to the fact that it can be removed via concentration on rotovap.




Common Uses:


Reagent for boc deprotections





Reagent for SEM deprotections





Reagent for benzyl deprotections




Reagent for PMB deprotections





Reagent for trityl deprotections




Reagent for THP deprotections





Reagent for the reduction of alcohols (TFA + Et3SiH)





Safety:


Trifluoroacetic acid (TFA) is an extremely corrosive acid which causes severe damage when in contact with skin, eyes, and tissue of mucous membrane.




References:


1) WO2010016005, page 83

2) WO2012149280, page 54

3) WO2016011390, page 105

4) WO2016011390, page 319

5) WO2016023832, page 41

6) Reich, H. J.; Rigby, J. H.; Handbook of Reagents for Organic Synthesis, Acidic and Basic Reagents

7) Wikipedia: Trifluoroacetic acid (link)

8) www.sigmaaldrich.com: Trifluoroacetic acid (link)