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Merck
CN

164623

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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24850091
EC Number:
248-214-5
Beilstein/REAXYS Number:
3574512
MDL number:
MFCD00013402
Assay:
97%

Key Documents

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InChI key

SQVQHTIKOZVGLR-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

97%

mp

~240 °C (dec.) (lit.)

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

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBF3371V
1126147V
1452402
1126147
05829AH

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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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