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164623

Sigma-Aldrich

Tropylium tetrafluoroborate

97%

Synonym(s):

Cycloheptatrienyl tetrafluoroborate, Tropylium fluoroborate

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About This Item

Empirical Formula (Hill Notation):
C7H7BF4
CAS Number:
27081-10-3
Molecular Weight:
177.94
Beilstein:
3574512
EC Number:
248-214-5
MDL number:
MFCD00013402
UNSPSC Code:
12352101
PubChem Substance ID:
24850091
NACRES:
NA.22

Assay

97%

mp

~240 °C (dec.) (lit.)

SMILES string

F[B-](F)(F)F.c1ccc[cH+]cc1

InChI

1S/C7H7.BF4/c1-2-4-6-7-5-3-1;2-1(3,4)5/h1-7H;/q+1;-1

InChI key

SQVQHTIKOZVGLR-UHFFFAOYSA-N

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Application

Reactant or reagent involved in:
  • Retro-Buchner reactions for synthesis of arylcyclopropanes
  • Desymmetrization for access to homocalystegine analogs or aminocycloheptitols
  • α-Cyanation of imines
  • Stereoselective α-alkylation of aldehydes with stable carbocations
  • Oxidative C-H activation of aliphatic aldehydes
  • Electrochemical Redox transformations

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)

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R B Banks et al.
Biochemical and biophysical research communications, 140(2), 609-615 (1986-10-30)
The stabilized carbonium ion salt, tropylium tetrafluoroborate, was oxidized to tropone (cycloheptatrienone) by rabbit liver aldehyde oxidase but not by the closely related molybdenum hydroxylase, xanthine oxidase. The tropylium cation is an aromatic hydrocarbon which lacks the aldehyde, imine, or

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