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683701

Sigma-Aldrich

6,7-Dihydro-2-pentafluorophenyl-5H-pyrrolo[2,1-c]-1,2,4-triazolium tetrafluoroborate

97%

Synonym(s):

2-(Pentafluorophenyl)-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium tetrafluoroborate 

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About This Item

Empirical Formula (Hill Notation):
C11H7BF9N3
CAS Number:
862095-91-8
Molecular Weight:
362.99
MDL number:
MFCD08459335
UNSPSC Code:
12352005
PubChem Substance ID:
329760869
NACRES:
NA.22

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

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)

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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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