Autorizzo l’utilizzo di cookies.

Accetto Utilizziamo cookies per migliorare il nostro servizio e realizzare statistiche. Questa funzione puó essere disattivata cambiando la configurazione del browser. Continuando a navigare senza modificare questi parametri, consideriamo che l’uso di cookies sia accettato

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
Aggiungi al carrello Aggiungi al preventivo generale Visualizza articolo

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). Immediately call a POISON CENTER/doctor

Altri riferimenti

Classe di rischio
Gruppo di imballaggio
Codice tariffe armonizzato


  • A10164

    Catechol, 99%
  • A12198

    Trifluoroacetic acid, 99%
  • A12646

    Triethylamine, 99%
  • 42578

    Palladium hydroxide, Pd 20% on carbon, nominally 50% water, Pearlman's Catalyst
  • 43741

    1-Methyl-2-pyrrolidinone, anhydrous, 99.5%, packaged under Argon in resealable ChemSeal™ bottles

Visualizzati di recente

Prodotti chimici

Scienze della vita

Metalli e materiali


Apparecchiature di analisi e di laboratorio