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Sigma-Aldrich

Ferrocenium tetrafluoroborate

technical grade

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Synonym(s):
Bis(cyclopentadienyl)iron tetrafluoroborate, Dicyclopentadienyliron fluoborate, Dicyclopentadienyliron tetrafluoroborate
Empirical Formula (Hill Notation):
C10H10BF4Fe
CAS Number:
1282-37-7
Molecular Weight:
272.84
MDL number:
MFCD00192174
UNSPSC Code:
12161600
PubChem Substance ID:
24871823
NACRES:
NA.22

grade

technical grade

Quality Level

100

reaction suitability

core: iron
reagent type: catalyst

mp

178 °C (dec.) (lit.)

SMILES string

[Fe+].F[B-](F)(F)F.[CH]1[CH][CH][CH][CH]1.[CH]2[CH][CH][CH][CH]2

InChI

1S/2C5H5.BF4.Fe/c2*1-2-4-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1

InChI key

ZSPXIHLQPWVOQR-UHFFFAOYSA-N

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General description

Ferrocenium tetrafluoroborate [FeCp2][BF4] is one of the commonly employed ferrocenium salts within chemical synthesis. Ferrocenium salts are commonly used as Lewis acid catalysts, one-electron oxidants, and electron donors.

Application

Ferrocenium tetrafluoroborate serves as:

  • an oxidizing agent in the synthesis of the monocationic Co(II)complex [CpCo(azpy)]+
  • a Lewis acid catalyst in epoxide ring opening and to activatethe carbonyl group for addition or cycloadditions reactions
  • an oxidizing agent when used in conjuntion with a Cl-source
  • a reversible redox reagent between stannole dianion and bistannole-1,2-dianion

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

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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Formation of exceptionally weak C?C bonds by metal-templated pinacol coupling
Folkertsma E., et al.
Dalton Transactions, 46, 6177?6182-6177?6182 (2017)
Reversible Redox Behavior between Stannole Dianion and Bistannole-1,2-Dianion
Ryuta Haga, Masaichi Saito, and Michikazu Yoshioka
Journal of the American Chemical Society, 128(15), 4934?4935-4934?4935 (2006)
Applications of ferrocenium salts in organic synthesis
Toma S, et al.
thieme, 1683-1695 (2015)
Fe (Cp) 2BF4: An efficient Lewis acid catalyst for the aminolysis of epoxides
Yadav GD, et al.
thieme, 629-634 (2014)
Protonation of a cobalt phenylazopyridine complex at the ligand yields a proton, hydride, and hydrogen atom transfer reagent
McLoughlin EA, et al.
Journal of the American Chemical Society, 140(41), 13233-13241 (2018)
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