683701
6,7-Dihydro-2-pentafluorophenyl-5H-pyrrolo[2,1-c]-1,2,4-triazolium tetrafluoroborate
97%
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Synonym(s):
2-(Pentafluorophenyl)-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium tetrafluoroborate
Empirical Formula (Hill Notation):
C11H7BF9N3
CAS Number:
Molecular Weight:
362.99
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
solid
reaction suitability
reagent type: catalyst
mp
245 °C
SMILES string
F[B-](F)(F)F.Fc1c(F)c(F)c(c(F)c1F)-[n+]2cn3CCCc3n2
InChI
1S/C11H7F5N3.BF4/c12-6-7(13)9(15)11(10(16)8(6)14)19-4-18-3-1-2-5(18)17-19;2-1(3,4)5/h4H,1-3H2;/q+1;-1
InChI key
KIWCIWCCQVTPOY-UHFFFAOYSA-N
Related Categories
Application
This triazolium catalyst is used for intermolecular homodimerization of aryl aldehydes, intramolecular aldehyde-ketone benzoin cyclizations, and intramolecular Stetter reations.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
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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Ming He et al.
Journal of the American Chemical Society, 128(26), 8418-8420 (2006-06-29)
Highly enantioselective, N-heterocyclic carbene (NHC)-catalyzed aza-Diels-Alder reactions are described. A novel chiral triazolium salt based on the cis-1,2-aminoindanol platform serves as an efficient precatalyst for the NHC-catalyzed redox generation of enolate dienophiles that undergo LUMOdiene-controlled Diels-Alder reactions with N-sulfonyl-alpha,beta-unsaturated imines
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