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674788

Sigma-Aldrich

5a(R),10b(S)-5a,10b-Dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate

97%

Synonym(s):

2-Pentafluorophenyl-6,10b-dihydro-4H,5aH-5-oxo-3,10c-diaza-2-azoniacyclopenta[c]fluorine tetrafluoroborate

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About This Item

Empirical Formula (Hill Notation):
C18H11BF9N3O
CAS Number:
872143-57-2
Molecular Weight:
467.10
MDL number:
MFCD08457666
UNSPSC Code:
12352005
PubChem Substance ID:
24885239
NACRES:
NA.22

Assay

97%

form

solid

mp

233-237 °C

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.Fc1c(F)c(F)c(c(F)c1F)-[n+]2c[n@@H]3[C@@H]4[C@@H](Cc5ccccc45)OCc3n2

InChI

1S/C18H11F5N3O.BF4/c19-12-13(20)15(22)18(16(23)14(12)21)26-7-25-11(24-26)6-27-10-5-8-3-1-2-4-9(8)17(10)25;2-1(3,4)5/h1-4,7,10,17H,5-6H2;/q+1;-1/t10-,17+;/m1./s1

InChI key

CPCMDOOTVHDRTM-CVJFODCESA-N

Application

5a(R),10b(S)-5a,10b-Dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate can be used as an N-heterocyclic carbene (NHC) organocatalyst in:
  • Benzoin reactions of aldehydes and total synthesis of a natural product named isodarparvinol B.
  • Synthesis of spirocyclic oxindole-dihydropyranones by reacting α-bromo-α,β-unsaturated aldehydes with isatin derivatives.
  • Synthesis of 1,4-dicarbonyl compounds through intramolecular Stetter reaction.

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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Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes
de Alaniz JR, et al.
The Journal of Organic Chemistry, 73(6), 2033-2040 (2008)
Minimization of Amounts of Catalyst and Solvent in NHC-Catalyzed Benzoin Reactions of Solid Aldehydes: Mechanistic Consideration of Solid-to-Solid Conversion and Total Synthesis of Isodarparvinol B
Iwai K, et al.
ACS Omega, 5(17), 10207-10216 (2020)
N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirocyclic oxindole--dihydropyranones
Xiao Z, et al.
Organic Letters, 16(14), 3632-3635 (2014)

Articles

Rovis Triazolium Catalyst

Rovis has demonstrated that triazolium salt in the presence of a base can act as an N-heterocyclic carbene organocatalyst in highly enantioselective intramolecular Stetter reactions.

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