Lanthanum trifluoromethanesulfonate Chemical Properties

Melting point:

>300°C

Density 

1.7

storage temp. 

Inert atmosphere,2-8°C

solubility 

sol H2O; partially sol THF, CH2Cl2; sparingly sol Et2O; insol hexane.

form 

Crystalline Powder

color 

White to light beige

Water Solubility 

Soluble in water.

Sensitive 

Hygroscopic

Hydrolytic Sensitivity

6: forms irreversible hydrate

BRN 

9009103

Stability:

hygroscopic

InChI

InChI=1S/3CHF3O3S.La/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

InChIKey

WGJJZRVGLPOKQT-UHFFFAOYSA-K

SMILES

C(F)(S([O-])(=O)=O)(F)F.C(F)(F)(F)S([O-])(=O)=O.C(F)(F)(F)S([O-])(=O)=O.[La+3]

CAS DataBase Reference

52093-26-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 1759 8/PG III

WGK Germany 

3

F 

3-10

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

28469099

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Lanthanum trifluoromethanesulfonate Usage And Synthesis

Description

Lanthanum trifluoromethanesulfonate is a Lewis acid catalyst useful for aldol, Michael, Diels-Alder, and other C-C bond forming reactions; also useful for preparing organolanthanum reagents, which react with hindered tertiary amides to afford ketones.

Chemical Properties

white to light beige crystalline powder

Uses

Lanthanum trifluoromethanesulfonate is a water-tolerant Lewis acid used in the Aldol reaction of silyl enol ethers with aldehydes. It is an effective catalyst for the Baylis-Hillman reaction. It also catalyzes Michael additions to methyl vinyl ketone in water.

reaction suitability

core: lanthanum
reagent type: catalyst

Synthesis

To an aqueous solution of triflic acid (50% v/v), a slight excess of lanthanum oxide (La2O3) is added; the resulting mixture is stirred for 15 min at rt and then filtered to remove the unreacted oxide; the filtrate is concentrated in vacuo at about 60 °C; residual water is removed by azeotropic distillation with toluene in vacuo to dryness; the resulting hydrate is placed in a flask equipped with a stirring bar, a stopcock filled with a glass wool plug, and a NaOH trap, and is then dehydrated by heating under vacuum (140 °C/0.1 mmHg or 180 °C/1.0 mmHg) for 16 h. The anhydrous Lanthanum trifluoromethanesulfonate La(OTf)3 is a white to gray-white solid.

storage

Anhydrous La(OTf)3 is hygroscopic and should be stored and weighed in a glove-box. Use in a fume hood.

Lanthanum trifluoromethanesulfonate(52093-26-2)Related Product Information

• INDIUM(III) TRIFLUOROMETHANESULFONATE
• Iron(III) trifluoromethanesulfonate
• Scandium trifluoromethanesulfonate
• Bis(tributyltin) oxide
• Sodium trifluoromethanesulfinate
• PALLADIUM(II) TRIFLUOROACETATE
• Bismuth(III) trifluoromethanesulfonate
• Lithium trifluoromethanesulfonate
• Zinc trifluoromethanesulfonate
• Aluminum trifluoromethanesulfonate
• Trifluoromethanesulfonic acid
• YTTERBIUM(III) TRIFLUOROMETHANESULFONATE HYDRATE
• Sodium trifluoromethanesulfonate
• Trifluoromethanesulfonic anhydride
• Trifluoromethanesulfonyl chloride
• SILVER TRIFLUOROMETHANESULFONATE
• Potassium trifluoromethanesulfonate
• 2-Bromoethyl trifluoromethanesulphonate