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
73602-61-6
Sinonimi
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

MDL
MFCD00043294
EINECS
277-550-5

Proprietà chimiche

Formula
C6H15N•3HF
Peso formula
161.21
Punto di fusione
-29°
Punto di ebollizione
70°/15mm
Punto di infiammabilità
87°(188°F)
Densità
0.990
Indice di rifrazione
1.3915
Sensibilità
Hygroscopic
Solubilità
Miscible with water, chloroform and hexanes.

Applicazioni

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.

Note

Hygroscopic. Incompatible with strong oxidizing agents and glass.

Letteratura

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

Beilstein
5522945
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2921.19
TSCA
Yes

Raccomandato

  • 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

Catalizzatori

Apparecchiature di analisi e di laboratorio