Triethylamine trihydrofluoride, ca 37% HF, Thermo Scientific Chemicals

Name: Triethylamine trihydrofluoride, ca 37% HF, Thermo Scientific Chemicals
SKU: L14417.14

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Catalog number L14417.14

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25 g

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Chemical Identifiers

CAS73602-61-6

IUPAC Nametrihydrogen triethylamine trifluoride

Molecular FormulaC6H18F3N

InChI KeyIKGLACJFEHSFNN-UHFFFAOYSA-N

SMILES[H+].[H+].[H+].[F-].[F-].[F-].CCN(CC)CC

Specifications

Specification Sheet

Assay from Supplier's CofA21.3-28.0% (w/w) 'free' HF content

Appearance (Color)Clear colorless to brown

Assay from Supplier's CofA32-43% total HF content

FormLiquid

Triethylamine trihydrofluoride acts as a mild and selective fluorinating agent used in the synthesis of acid fluorides and alkyl fluorides. It is also used in the synthesis of vicinal difluorides from epoxides, 3-fluoroazetidine. It is utilized as a selective reagent for the cleavage of O-silyl groups in carbohydrates, nucleotides and cyanohydrins. It is actively involved in the electrochemical fluorodeiodination of alkyl iodides and fluorodesilylation in beta-lactams.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Triethylamine trihydrofluoride acts as a mild and selective fluorinating agent used in the synthesis of acid fluorides and alkyl fluorides. It is also used in the synthesis of vicinal difluorides from epoxides, 3-fluoroazetidine. It is utilized as a selective reagent for the cleavage of O-silyl groups in carbohydrates, nucleotides and cyanohydrins. It is actively involved in the electrochemical fluorodeiodination of alkyl iodides and fluorodesilylation in beta-lactams.

Solubility
Miscible with water, chloroform and hexanes.

Notes
Hygroscopic. Incompatible with strong oxidizing agents and glass.

RUO – Research Use Only

General References:

Convenient mild fluorinating agent which can be handled in glass equipment (long-term storage in glass is not recommended):
Activated halides can be displaced to give the corresponding fluorides J. Fluorine Chem., 15, 423 (1980); 47, 467 (1990). Carbohydrate bromides or mesylates can be converted to fluorinated analogues with inversion of configuration: J. Fluorine Chem., 60, 49 (1993); Tetrahedron Lett., 31, 6527 (1990).
In the presence of NBS, alkenes undergo trans-fluorobromination in high yield: Synthesis, 562 (1987); Liebigs Ann. Chem., 849 (1995); Org. Synth., 76, 159 (1998). Vinyl oxiranes undergo ring opening to give fluorohydrins: J. Fluorine Chem., 70, 1 (1995); in the presence of NBS, fluorobromination of the double bond occurs instead: J. Org. Chem., 59, 5277 (1994).
A variety of compounds undergo electrochemical fluorination at activated positions. ɑ-Fluorinations of sulfides have been extensively studied by Fuchigami and others. The reaction usually requires the presence of an electron withdrawing group ɑ- to the sulfur atom, e.g. monofluorination of ethyl (phenylthio)acetate: J. Org. Chem., 56, 6731 (1991); 59, 5937 (1994); 60, 3459 (1995), and of phenylthio substituted nitrogen heterocycles including ß-lactams: Tetrahedron Lett., 33, 7017 (1992); J. Org. Chem., 57, 3755 (1992); 58, 4200 (1993).
For electrochemical fluorodeiodination of alkyl iodides, see: Synlett, 999 (2000). Fluorodesilylation in ß-lactams has also been reported: J. Chem. Soc., Perkin 1, 1327 (1995).