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Sigma-Aldrich

Ferrocenium tetrafluoroborate

technical grade

Synonym(s):

Bis(cyclopentadienyl)iron tetrafluoroborate, Dicyclopentadienyliron fluoborate, Dicyclopentadienyliron tetrafluoroborate

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About This Item

Empirical Formula (Hill Notation):
C10H10BF4Fe
CAS Number:
Molecular Weight:
272.84
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

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

Signal Word

Danger

Hazard Statements

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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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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