[L14417] CAS 73602-61-6 | Triethylamine trihydrofluoride, ca 37% HF

CAS : 73602-61-6
UN# : UN1790
MDL : MFCD00043294
Hazard Class : 8
EINECS : 277-550-5
Packing Group : II

Other name :

Hydrogen fluoride triethylamineTriethylamine tris(hydrogen fluoride)

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. Store under Nitrogen. Ambient temperatures.
Form : Liquid
Solubility : Miscible with water, chloroform and hexanes.

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).

Notes

Hygroscopic. Incompatible with strong oxidizing agents and glass.Other References:Beilstein: 5522945UN#: UN1790

Grade Specifications

Grade Specifications

Hazard Statements : H300-H310-H330-H314-H318-H227Fatal 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-P310Wear 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.