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Names | |
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IUPAC name
Ferrocenecarboxylic acid
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Other names
Ferrocenemonocarboxylic acid
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Identifiers | |
3D model (
JSmol)
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ChemSpider | |
ECHA InfoCard | 100.013.673 |
PubChem
CID
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CompTox Dashboard (
EPA)
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Properties | |
C11H10FeO2 | |
Molar mass | 230.044 g·mol−1 |
Appearance | yellow solid |
Density | 1.862 g/cm3 [1] |
Melting point | 214–216 °C (417–421 °F; 487–489 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Ferrocenecarboxylic acid is the organoiron compound with the formula (C5H5)Fe(C5H4CO2H). It is the simplest carboxylic acid derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis. [2]
The pKa of ferrocenecarboxylic acid is 7.8. The acidity increases more than a thousand-fold, to pH 4.54 upon oxidation to the ferrocenium cation. [3]
By treatment with thionyl chloride, the carboxylic acid anhydride ([(C5H5)Fe(C5H4CO)]2O) is produced. [4] [5]
Derivatives of ferrocenecarboxylic acid are components of some redox switches.
![]() | |
Names | |
---|---|
IUPAC name
Ferrocenecarboxylic acid
| |
Other names
Ferrocenemonocarboxylic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.013.673 |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C11H10FeO2 | |
Molar mass | 230.044 g·mol−1 |
Appearance | yellow solid |
Density | 1.862 g/cm3 [1] |
Melting point | 214–216 °C (417–421 °F; 487–489 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Ferrocenecarboxylic acid is the organoiron compound with the formula (C5H5)Fe(C5H4CO2H). It is the simplest carboxylic acid derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis. [2]
The pKa of ferrocenecarboxylic acid is 7.8. The acidity increases more than a thousand-fold, to pH 4.54 upon oxidation to the ferrocenium cation. [3]
By treatment with thionyl chloride, the carboxylic acid anhydride ([(C5H5)Fe(C5H4CO)]2O) is produced. [4] [5]
Derivatives of ferrocenecarboxylic acid are components of some redox switches.