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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

CAS Number
73602-61-6
Synonyms
Hydrogen fluoride triethylamine
Triethylamine tris(hydrogen fluoride)

Size Price ($) Quantity Availability
5g 15.72
25g 49.65
100g 148.66
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Triethylamine trihydrofluoride, ca 37% HF

MDL
MFCD00043294
EINECS
277-550-5

Chemical Properties

Formula
C6H15N•3HF
Formula Weight
161.21
Melting point
-29°
Boiling Point
70°/15mm
Flash Point
87°(188°F)
Density
0.990
Refractive Index
1.3915
Sensitivity
Hygroscopic
Solubility
Miscible with water, chloroform and hexanes.

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.

Notes

Hygroscopic. Incompatible with strong oxidizing agents and glass.

Literature 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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H310-H330-H314-H318-H227

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

Precautionary Statements: P280-P303+P361+P353-P305+P351+P338-P320-P310

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 or doctor/physician.

Other References

Beilstein
5522945
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2921.19
TSCA
Yes

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