FERROCENECARBOXYLIC ACID
FERROCENECARBOXYLIC ACID
Ferrocenecarboxylic acid is the organoiron compound with the formula (C5H5)Fe(C5H4CO2H).
Ferrocenecarboxylic acid is the simplest carboxylic acid derivative of ferrocene.
Ferrocenecarboxylic acid can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis.
CAS Number: 1271-42-7
EC Number: 215-040-6
Molecular Formula: C11H10FeO2
Molecular Weight (g/mol): 230.04
Synonyms: Ferrocene carboxylic acid, Carboxyferrocene, Bis(cyclopentadienyl)iron(II) carboxylate, Iron(II) biscyclopentadienyl carboxylate, FcCOOH (Abbreviation using chemical symbols), Iron(II) cyclopentadienylcarboxylate, Cyclopentadienyliron dicarboxylate, Iron dicyclopentadienyl carboxylate, Ferrocenylcarboxylic acid, Ferrocenecarboxylic acid, Ferrocene carboxylic acid, Carboxyferrocene, Bis(cyclopentadienyl)iron(II) carboxylate, Iron(II) biscyclopentadienyl carboxylate, FcCOOH (Abbreviation using chemical symbols), Iron(II) cyclopentadienylcarboxylate, Cyclopentadienyliron dicarboxylate, Iron dicyclopentadienyl carboxylate, Ferrocenylcarboxylic acid, 1,3-Cyclopentadiene-1-carboxylic acid, compd. with 1,3-cyclopentadiene, iron salt (1:1:1) [ACD/Index Name], Ferrocenecarboxylic acid, 1271-42-7 [RN]
Ferrocenecarboxylic Acid is generally immediately available in most volumes.
High purity, submicron and nanopowder forms may be considered.
Ferrocenecarboxylic acid is a widely used stain in cytopathology.
Ferrocenecarboxylic acid is a polychrome stain that has the ability to stain several constituents of cell differentially due to the presence of multiple dyes.
Ferrocenecarboxylic acid stain consists of a basic dye, haematoxylin that stains the nucleus and three acid dyes like light green, eosin and orange G that stain the cytoplasm.
Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS.
Ferrocenecarboxylic acid is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
Ferrocene carboxylic acid (FCCa) is an organometallic compound comprised of a ferrocene core with a carboxylic acid functional group.
Ferrocenecarboxylic acid is used as a mediator in electrocatalytic oxidation.
Due to its excellent redox properties, Ferrocenecarboxylic acid is widely used in electrochemistry, redox probes, and peptide chain modifications.
In addition, a direct cross-coupling reaction was explored using ferrocenecarboxylic acid and alkenes.
Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS.
Ferrocenecarboxylic acid is an intermediate that applicated in organic synthesis, pharmaceuticals, agrochemicals, and dyestuffs.
The synthesis of this product is described in the literature.
Ferrocenecarboxylic acid, a versatile chemical compound, finds wide-ranging applications across various fields.
Ferrocenecarboxylic acid is a metal-organic compound characterized by the connection of two ferrocene molecules through a carboxy ligand.
Notably, ferrocene stands as a stable yet highly reactive metal-organic compound that has been extensively researched due to its potential applications in catalysis, materials science, and medicine.
In scientific research, Ferrocenecarboxylic acid plays a pivotal role across multiple domains.
Ferrocenecarboxylic acid serves as a catalyst in catalysis, facilitating the synthesis of diverse compounds through polymerization, oxidation, and reduction reactions.
In materials science, Ferrocenecarboxylic acid acts as a fundamental molecular building block for the synthesis of polymers and nanomaterials.
Although the precise mechanism of action of Ferrocenecarboxylic acid remains to be fully elucidated, Ferrocenecarboxylic acid is believed that the carboxy ligand binds to the ferrocene molecules, forming a stable complex.
This complex, in turn, engages with other molecules, including proteins, to facilitate an array of reactions.
Ferrocenecarboxylic acid is an intriguing compound in organometallic chemistry, featuring a unique structural motif that combines the classical metallocene architecture of ferrocene with a carboxylic acid functionality.
Ferrocenecarboxylic acid’s chemical formula is C11H10FeO2.
The structure of ferrocenecarboxylic acid consists of a central iron (Fe) atom sandwiched between two cyclopentadienyl (Cp) rings, forming the well-known ferrocene moiety.
Additionally, one of the cyclopentadienyl rings is appended with a carboxylic acid group (-COOH).
This attachment creates a molecular framework where the iron atom is connected to a carbon atom of the cyclopentadienyl ring and to an oxygen atom of the carboxylic acid group.
The synthesis of ferrocenecarboxylic acid typically involves the reaction of ferrocene with an appropriate carboxylation reagent, such as carbon dioxide or carbon monoxide, under suitable conditions.
The resulting product is then typically purified and characterized using various analytical techniques, including spectroscopic methods like nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.
Ferrocenecarboxylic acid has been explored for its reactivity in a variety of chemical transformations.
Ferrocenecarboxylic acid serves as a precursor or starting material for the synthesis of diverse ferrocene derivatives, where the carboxylic acid group can undergo various functionalization reactions, such as esterification, amidation, or metalation.
These derivatives may exhibit interesting properties and find applications in fields ranging from catalysis and materials science to medicinal chemistry and molecular electronics.
Furthermore, ferrocenecarboxylic acid and its derivatives have been investigated for their potential use in electrochemical applications due to the redox-active nature of the ferrocene unit.
They may serve as components in redox-active materials, sensors, or molecular devices, exploiting the reversible oxidation and reduction processes of the ferrocene moiety.
Overall, ferrocenecarboxylic acid represents an important building block in the realm of organometallic chemistry, offering a rich playground for the exploration of novel structures, reactivities, and applications within the broader context of metal-centered molecular chemistry.
Applications of Ferrocenecarboxylic acid:
Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS.
Ferrocenecarboxylic acid is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
Ferrocene carboxylic acid can be used as a:
Starting material in the synthesize of ferrocene-guanine conjugates.
Redox mediator in electrochemical-chemical-chemical (ECC) redox cycling.
Purification Methods of Ferrocenecarboxylic acid:
Ferrocenecarboxylic acid crystallises as yellow crystals from pet ether (m 225-230odec), CHCl3 (m 208.5odec), toluene/pet ether (m 195-205odec), or aqueous ethanol.
The methyl ester crystallises from aqueous MeOH with m 70-71o.
The anhydride has m 143-145o when recrystallised from pet ether.
The amide has m 168-170o when crystallised from CHCl3/Et2O or m 167-169o when crystallised from *C6H6/MeOH.
Reactions and derivatives of Ferrocenecarboxylic acid:
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.
By treatment with thionyl chloride, the carboxylic acid anhydride ([(C5H5)Fe(C5H4CO)]2O) is produced.
Derivatives of ferrocenecarboxylic acid are components of some redox switches.
Handling and storage of Ferrocenecarboxylic acid:
Precautions for safe handling:
Advice on protection against fire and explosion:
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Store in cool place.
Keep container tightly closed in a dry and well-ventilated place.
Storage class:
Storage class (TRGS 510):11: Combustible Solids
Stability and reactivity of Ferrocenecarboxylic acid:
Reactivity:
No data available
Chemical stability:
Stable under recommended storage conditions.
Possibility of hazardous reactions:
No data available
Conditions to avoid:
No data available
Incompatible materials:
Strong oxidizing agents
First aid measures of Ferrocenecarboxylic acid:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
In case of skin contact:
Wash off with soap and plenty of water.
In case of eye contact:
Flush eyes with water as a precaution.
If swallowed:
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Indication of any immediate medical attention and special treatment needed:
No data available
Firefighting measures of Ferrocenecarboxylic acid:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture:
Carbon oxides
Iron oxides
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Further information:
No data available
Accidental release measures of Ferrocenecarboxylic acid:
Personal precautions, protective equipment and emergency procedures:
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions:
No special environmental precautions required.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Exposure controls/personal protection of Ferrocenecarboxylic acid:
Personal protective equipment:
Eye/face protection:
Use equipment for eye protection tested and approved under appropriate
government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove removal technique (without touching glove’s outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of Regulation (EU) 2016/425 and the standard EN 374 derived from it.
Body Protection:
Choose body protection in relation to Ferrocenecarboxylic acid’s type, to the concentration and amount of angerous substances, and to the specific work-place.
The type of protective quipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Respiratory protection is not required.
Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure:
No special environmental precautions required.
Identifiers of Ferrocenecarboxylic acid:
CAS Number: 1271-42-7
ChemSpider: 26585892
ECHA InfoCard: 100.013.673
PubChem CID: 15764230
CompTox Dashboard (EPA): DTXSID40925783
InChI: InChI=1S/C6H5O2.C5H5.Fe/c7-6(8)5-3-1-2-4-5;1-2-4-5-3-1;/h1-4H,(H,7,8);1-5H;/q2*-1;+2
Key: BAJHDUZEIKRKAS-UHFFFAOYSA-N
SMILES: [CH-]1C=CC=C1.C1=C[C-](C=C1)C(=O)O.[Fe+2]
CAS: 1271-42-7
Molecular Formula: C11H10FeO2
Molecular Weight (g/mol): 230.04
MDL Number: MFCD00001430
InChI Key: OUPWBVGTMCICLR-UHFFFAOYSA-N
Synonym: Carboxyferrocene; (Carboxycyclopentadienyl)cyclopentadienylironShow More
IUPAC Name: Ferrocenecarboxylic acid
SMILES: [Fe].c1cccc1.OC(=O)c1cccc1
Empirical Formula (Hill Notation): C11H10FeO2
CAS Number: 1271-42-7
Molecular Weight: 230.04
EC Number: 215-040-6
MDL number: MFCD00001430
PubChem Substance ID: 24846745
NACRES: NA.22
Product Number: F0165
Purity / Analysis Method: >98.0%(T)(HPLC)
Molecular Formula / Molecular Weight: C__1__1H__1__0FeO__2 = 230.04
Physical State (20 deg.C): Solid
Packaging and Container: 1G-Glass Bottle with Plastic Insert (View image)
CAS RN: 1271-42-7
PubChem Substance ID: 125309342
SDBS (AIST Spectral DB): 6892
MDL Number: MFCD00001430
Properties of Ferrocenecarboxylic acid:
Chemical formula: 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)
Assay: 97%
reaction suitability:
core: iron
reagent type: catalyst
mp: 210 °C (dec.) (lit.)
SMILES string: [Fe].[CH]1[CH][CH][CH][CH]1.OC(=O)[C]2[CH][CH][CH][CH]2
InChI: 1S/C6H5O2.C5H5.Fe/c7-6(8)5-3-1-2-4-5;1-2-4-5-3-1;/h1-4H,(H,7,8);1-5H;
InChI key: VUJLGCHOGQEAED-UHFFFAOYSA-N
Related compounds: 1,1′-Ferrocenedicarboxylic acid
grade: purum
Quality Level: 200
Assay: ≥96%
reaction suitability:
core: iron
reagent type: catalyst
mp: 210 °C (dec.) (lit.)
SMILES string: [Fe].[CH]1[CH][CH][CH][CH]1.OC(=O)[C]2[CH][CH][CH][CH]2
InChI: 1S/C6H5O2.C5H5.Fe/c7-6(8)5-3-1-2-4-5;1-2-4-5-3-1;/h1-4H,(H,7,8);1-5H;
InChI key: VUJLGCHOGQEAED-UHFFFAOYSA-N
Specifications of Ferrocenecarboxylic acid:
Melting Point: ∼210°C (decomposition)
Quantity: 1 g
Solubility Information: Insoluble in water.
Formula Weight: 230.05
Percent Purity: 98%
Chemical Name or Material: Ferrocenecarboxylic acid
Molecular Weight: 230.04 g/mol
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 8
Rotatable Bond Count: 1
Exact Mass: 230.003015 g/mol
Monoisotopic Mass: 230.003015 g/mol
Topological Polar Surface Area: 37.3Ų
Heavy Atom Count: 14Complexity: 198
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 3
Compound Is Canonicalized: Yes
Names of Ferrocenecarboxylic acid:
IUPAC name:
Ferrocenecarboxylic acid
Other name:
Ferrocenemonocarboxylic acid