Synlett 2010(19): 2971-2972  
DOI: 10.1055/s-0030-1258840
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

2,2,2-Trifluoroethanol

Hartmut Schwertfeger*
Institut für Organische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Gießen, Germany
e-Mail: [email protected];
Further Information

Publication History

Publication Date:
22 October 2010 (online)

Introduction

2,2,2-Trifluoroethanol (TFE) is one of the most common used fluorinated alcohols that is available on large commercial scale. In contrast to its non-fluorinated analogue, TFE has a lower boiling point (74 ˚C) and is more acidic (pKa 12.4). [¹] Due to its low boiling point TFE can easily be removed from reaction mixtures by destillation. TFE can be prepared by reduction of trifluoroacetamide [²] or trifluoroacetic acid [³] with H2 and various catalysts. Another possibility is the treatment of trifluoroacetyl chloride [4] and n-butyl trifluoroacetate [5] using LiAlH4 (Scheme  [¹] ). Owing to its unique properties TFE has been used in a variety of reactions as a solvent, cosolvent or additive, [¹] but it can also be utilized as a reagent for the introduction of a fluorine moiety.

Scheme 1 Preparation of 2,2,2-trifluoroethanol

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