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515884

Sigma-Aldrich

Aluminum trifluoromethanesulfonate

99.9% trace metals basis

Synonym(s):

Aluminum tris(trifluoromethanesulfonate), Tris(trifluoromethanesulfonato)aluminum, Aluminum triflate

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About This Item

Linear Formula:
(CF3SO3)3Al
CAS Number:
74974-61-1
Molecular Weight:
474.19
MDL number:
MFCD00143596
UNSPSC Code:
12161600
PubChem Substance ID:
24873851
NACRES:
NA.22

Assay

99.9% trace metals basis

reaction suitability

core: aluminum
reagent type: catalyst

mp

300 °C (lit.)

SMILES string

[Al+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

InChI

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

InChI key

FKOASGGZYSYPBI-UHFFFAOYSA-K

Application

Aluminum trifluoromethanesulfonate (aluminum triflate or Al(OTf)3) can be employed as a catalyst:
  • In the regioselective synthesis of cyclic ethers by cycloisomerization of unsaturated alcohols.
  • In the conversion of saccharides into 5-hydroxymethylfurfural (5-HMF).
  • Along with Pd(OAc)2/BINAP for the methoxycarbonylation reaction of phenylacetylene.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Valorization of an underused sugar derived from hemicellulose: Efficient synthesis of 5-hydroxymethylfurfural from mannose with aluminum salt catalyst in dimethyl sulfoxide/water mixed solvent
Jia S, et al.
Royal Society of Chemistry Advances, 7(62), 39221-39227 (2017)
Aluminium (III) trifluoromethanesulfonate as an efficient catalyst for the intramolecular hydroalkoxylation of unactivated olefins: experimental and theoretical approaches
Coulombel L, et al.
Chemistry?A European Journal , 12(24), 6356-6365 (2006)
Recyclable Pd (OAc) 2/Ligand/Al (OTf) 3 Catalyst for the Homogeneous Methoxycarbonylation and Hydrocarboxylation Reactions of Phenylacetylene
Williams DBG, et al.
Organometallics, 30(18), 4968-4973 (2011)
Shaochen Zhang et al.
Science (New York, N.Y.), 364(6435), 45-51 (2019-04-06)
Accessing enantiomerically enriched amines often demands oxidation-state adjustments, protection and deprotection processes, and purification procedures that increase cost and waste, limiting applicability. When diastereomers can be formed, one isomer is attainable. Here, we show that nitriles, largely viewed as insufficiently
Yusuke Imazaki et al.
Journal of the American Chemical Society, 134(36), 14760-14763 (2012-08-25)
Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)(3)]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition
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