Lanthanum triflate

Lanthanum triflate
Names
IUPAC name
Lanthanum(III) trifluoromethanesulfonate
Other names
  • La(OTf)3
  • Lanthanum tris(trifluoromethanesulfonate)
  • Tris(trifluoromethanesulfonato)lanthanum
  • Lanthanum(III) triflate
  • Trifluoromethanesulfonic acid lanthanum salt
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.917
EC Number
  • 628-666-3
  • InChI=1S/3CHF3O3S.La/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
    Key: WGJJZRVGLPOKQT-UHFFFAOYSA-K
  • nonahydrate: InChI=1S/3CHF3O3S.La.9H2O/c3*2-1(3,4)8(5,6)7;;;;;;;;;;/h3*(H,5,6,7);;9*1H2/q;;;+3;;;;;;;;;/p-3
    Key: DDAPLPNUENWYHJ-UHFFFAOYSA-K
  • [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F
  • nonahydrate: C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].O.O.O.O.O.O.O.O.O.[La+3]
Properties
CF9LaO9S3
Molar mass 562.07 g·mol−1
Appearance white to gray–white solid
Density 1.7 g/cm3
Melting point 300 °C (572 °F; 573 K)
soluble
Hazards
GHS labelling:[1]
GHS05: Corrosive
Danger[2]
H314
P260, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Lanthanum triflate is a complex inorganic compound of lanthanum, fluorine, carbon, sulphur, and oxygen with the chemical formula (CF3SO3)3La.[3] This is the lanthanum salt of trifluoromethanesulphonic acid.

Synthesis

Lanthanum triflate is typically synthesized by reacting lanthanum oxide with 50% aqueous trifluoromethanesulfonic acid under heating.[4]

La2O3 + 6HOTf → 2La(OTf)3 + 3H2O

Physical properties

The compound forms white to gray-white solid. It is soluble in water; partially soluble in tetrahydrofuran (THF) and dichloromethane; sparingly soluble in diethyl ether; and insoluble in hexane.

Like other lanthanide triflates, lanthanum triflate is a Lewis acid, but unlike other Lewis acids like AlCl3, it is stable in water.[5]

Uses

The compound serves as an efficient standalone catalyst for the direct synthesis of various amides from esters and amines under gentle reaction conditions.[6][7]

References

  1. ↑ "Lanthan(III)-Trifluormethanesulfonate >98.0%". tcichemicals.com. Retrieved 7 May 2026.
  2. ↑ "Lanthanum(III) Trifluoromethanesulfonate | CymitQuimica". cymitquimica.com. Retrieved 7 May 2026.
  3. ↑ "Lanthanum(III) trifluoromethanesulfonate". Sigma Aldrich. Retrieved 7 May 2026.
  4. ↑ Forsberg, John H.; Spaziano, Vincent T.; Balasubramanian, Trichey M.; Liu, Gordon K.; Kinsley, Steven A.; Duckworth, Charles A.; Poteruca, John J.; Brown, Paul S.; Miller, Judith L. (March 1987). "Use of lanthanide(III) ions as catalysts for the reactions of amines with nitriles". The Journal of Organic Chemistry. 52 (6): 1017–1021. doi:10.1021/jo00382a009.
  5. ↑ Kobayashi, Shū; Sugiura, Masaharu; Kitagawa, Hidetoshi; Lam, William W.-L. (1 June 2002). "Rare-Earth Metal Triflates in Organic Synthesis". Chemical Reviews. 102 (6): 2227–2302. Bibcode:2002ChRv..102.2227K. doi:10.1021/cr010289i. PMID 12059268.
  6. ↑ Morimoto, Hiroyuki; Fujiwara, Risa; Shimizu, Yuhei; Morisaki, Kazuhiro; Ohshima, Takashi (4 April 2014). "Lanthanum(III) Triflate Catalyzed Direct Amidation of Esters". Organic Letters. 16 (7): 2018–2021. doi:10.1021/ol500593v. PMID 24660939. Retrieved 7 May 2026.
  7. ↑ Hong, Yaping; Collins, Scott (15 April 2001). "Lanthanum(III) Triflate". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289X.rl003. ISBN 0-471-93623-5. Retrieved 7 May 2026.{{cite journal}}: CS1 maint: periodical has ISBN (link)
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