Triethylamine trihydrofluoride

• Catalog No.: L14417
• CAS Number: 73602-61-6
• M. F.: C6H18F3N
• M. W.: 161.2090296
• Purity: ca 37% HF

SYNONYMS

• Title: 三乙胺三氢氟酸盐
• IUPAC name: triethylazanium fluoride dihydrofluoride
• IUPAC Traditional name: TEAH fluoride dihydrofluoride
• Synonyms: Triethylamine tris(hydrogen fluoride); Hydrogen fluoride triethylamine

DATABASE IDS

• CAS Number: 73602-61-6
• EC Number: 277-550-5
• MDL Number: MFCD00043294
• Beilstein Number: 5522945

PROPERTIES

• Purity: ca 37% HF
• Boiling Point: 70°C/15mm
• Density: 0.990
• Flash Point: 87°C(188°F)
• Melting Point: -29°C
• Refractive Index: 1.3915
• GHS Hazard statements: H300-H310-H330-H314-H318-H227
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P320-P310
• Risk Statements: 26/27/28-35
• Safety Statements: 26-27/28-36/37/39-45-60
• Storage Warning: Hygroscopic
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN1790
• Packing Group: II

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 ?-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 ?-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).