164623

Sigma-Aldrich

Tropylium tetrafluoroborate

97%

Synonym(s):
Cycloheptatrienyl tetrafluoroborate, Tropylium fluoroborate
Empirical Formula (Hill Notation):
C7H7BF4
CAS Number:
Molecular Weight:
177.94
Beilstein/REAXYS Number:
3574512
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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

Packaging

10 g in amber poly bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3261 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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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