PRODUCTS

CARBOXYFERROCENE

Carboxyferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4CO2H).
Carboxyferrocene is the simplest carboxylic acid derivative of ferrocene.
Carboxyferrocene 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]

Carboxyferrocene is generally immediately available in most volumes.
High purity, submicron and nanopowder forms may be considered.

Carboxyferrocene is a widely used stain in cytopathology.
Carboxyferrocene is a polychrome stain that has the ability to stain several constituents of cell differentially due to the presence of multiple dyes.
Carboxyferrocene 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.

Carboxyferrocene is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS.
Carboxyferrocene 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.
Carboxyferrocene is used as a mediator in electrocatalytic oxidation.

Due to its excellent redox properties, Carboxyferrocene is widely used in electrochemistry, redox probes, and peptide chain modifications.
In addition, a direct cross-coupling reaction was explored using Carboxyferrocene and alkenes.

Carboxyferrocene is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS.
Carboxyferrocene is an intermediate that applicated in organic synthesis, pharmaceuticals, agrochemicals, and dyestuffs.
The synthesis of this product is described in the literature.

Carboxyferrocene, a versatile chemical compound, finds wide-ranging applications across various fields.
Carboxyferrocene 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, Carboxyferrocene plays a pivotal role across multiple domains.

Carboxyferrocene serves as a catalyst in catalysis, facilitating the synthesis of diverse compounds through polymerization, oxidation, and reduction reactions.
In materials science, Carboxyferrocene acts as a fundamental molecular building block for the synthesis of polymers and nanomaterials.

Although the precise mechanism of action of Carboxyferrocene remains to be fully elucidated, Carboxyferrocene 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.

Carboxyferrocene 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.
Carboxyferrocene's chemical formula is C11H10FeO2.

The structure of Carboxyferrocene 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 Carboxyferrocene 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.

Carboxyferrocene has been explored for its reactivity in a variety of chemical transformations.
Carboxyferrocene 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, Carboxyferrocene 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, Carboxyferrocene 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 Carboxyferrocene:
Carboxyferrocene is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS.
Carboxyferrocene 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 Carboxyferrocene:
Carboxyferrocene 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 Carboxyferrocene:
The pKa of Carboxyferrocene 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 Carboxyferrocene are components of some redox switches.

Handling and storage of Carboxyferrocene:

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 Carboxyferrocene:

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 Carboxyferrocene:

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 Carboxyferrocene:

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 Carboxyferrocene:

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 Carboxyferrocene:

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 Carboxyferrocene'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 Carboxyferrocene:
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: Ferrocenecarboxylic acid; (Carboxycyclopentadienyl)cyclopentadienyliron
IUPAC Name: Carboxyferrocene
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 Carboxyferrocene:
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

Specifications of Carboxyferrocene:
Melting Point: ∼210°C (decomposition)
Quantity: 1 g
Solubility Information: Insoluble in water.
Formula Weight: 230.05
Percent Purity: 98%
Chemical Name or Material: Carboxyferrocene

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: 37.3Å²
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 Carboxyferrocene:

IUPAC name:
Carboxyferrocene

Other name:
Ferrocenemonocarboxylic acid