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73602-61-6 - Triethylamine trihydrofluoride, ca 37% HF - Hydrogen fluoride triethylamine - Triethylamine tris(hydrogen fluoride) - L14417 - Alfa Aesar

L14417 Triethylamine trihydrofluoride, ca 37% HF

Codice CAS
Hydrogen fluoride triethylamine
Triethylamine tris(hydrogen fluoride)

Dimensioni Prezzo ($) Quantità Disponibilità
5g 16,70
25g 49,90
100g 159,00
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Triethylamine trihydrofluoride, ca 37% HF


Proprietà chimiche

Peso formula
Punto di fusione
Punto di ebollizione
Punto di infiammabilità
Indice di rifrazione
Miscible with water, chloroform and hexanes.


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.


Hygroscopic. Incompatible with strong oxidizing agents and glass.


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).

Excellent, selective reagent for cleavage of O-silyl groups in carbohydrates, nucleotides, cyanohydrins, etc.: Carbohydr. Res., 166, 309 (1987); J. Org. Chem., 52, 564 (1987); Bioorg. Chem. Med. Lett., 4, 1345 (1994); J. Am. Chem. Soc., 116, 4697 (1994). This has been exploited in a mild synthesis of substituted furans: Tetrahedron Lett., 37, 6065 (1996):

The Balz-Schiemann reaction of aryldiazonium fluoroborates with the reagent under ultrasound irradiation gives improved yields of aryl fluorides: Z. Chem., 26, 169 (1986).

For a review of the use of the reagent in synthesis, see: J. Prakt. Chem./ Chem. Ztg., 338, 99 (1996).

Carpentier, C.; Godbout, R.; Otis, F.; Voyer, N. Synthesis and use of N-Fmoc-l-fluoroalanine. Tetrahedron Lett. 2015, 56 (10), 1244-1246.

Hua, G.; Du, J.; Surgenor, B. A.; Slawin, A. M.; Woollins, J. D. Novel Fluorinated Phosphorus-Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl-and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters. Molecules 2015, 20 (7), 12175-12197.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227-H300-H310-H330-H314-H318

Combustible liquid. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P280-P303+P361+P353-P305+P351+P338-P320-P310a

Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label).

Altri riferimenti

Classe di rischio
Gruppo di imballaggio
Codice tariffe armonizzato


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