Ferrocenecarboxylic acid Chemical Properties

Melting point:

210 °C (dec.)(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)

form 

crystal

color 

yellow

Water Solubility 

Insoluble in water.

Exposure limits

ACGIH: TWA 1 mg/m3
NIOSH: TWA 1 mg/m3

Stability:

Stable. Incompatible with strong oxidizing agents.

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;

InChIKey

VUJLGCHOGQEAED-UHFFFAOYSA-N

SMILES

[C]1(C(=O)O)[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe] |^1:0,4,5,6,7,8,9,10,11,12|

CAS DataBase Reference

1271-42-7(CAS DataBase Reference)

NIST Chemistry Reference

Ferrocene carboxylic acid(1271-42-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

29319090

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ferrocenecarboxylic acid Usage And Synthesis

Description

Ferrocenecarboxylic acid is a metal-organic compound characterized by connecting two ferrocene molecules through a carboxy ligand. Notably, ferrocene is a stable yet highly reactive metal-organic compound that has been extensively researched due to its potential applications in catalysis, materials science, and medicine. It serves as a catalyst in catalysis, facilitating the synthesis of diverse compounds through polymerization, oxidation, and reduction reactions. In materials science, it acts as a fundamental molecular building block for synthesizing polymers and nanomaterials. Although the precise mechanism of action of Ferrocenecarboxylic acid remains fully elucidated, it 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 various reactions[1-2].

Chemical Properties

dark brown powder

Uses

Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Uses

Ferrocenecarboxylic acid (FCA) is a multifunctional organic reagent with applications in the following areas:
(1) As a synthetic precursor: synthesising amino-MIL-53(Al) through the adsorption of ferrocene and FCA. Amino-MIL-53(Al) is an amino-functionalised derivative of the metal-organic framework MIL-53(Al).
(2) As a chemical additive: Employed in preparing electrode materials and for the electrocatalytic oxidation of NADH.
(3) Based on Fca, ferrocenecarboxylic acid-capped pillar[5]arene (FACP5) was synthesised as a guest molecule. This interacts with the host molecule, a galactose derivative (G), to form a supramolecular vesicle system suitable for targeted drug delivery.
(4) Fca serves as the key substance generating electrical signals in electrochemical sensors for prostate-specific antigen (PSA) detection. This sensor is suitable for the early clinical diagnosis of prostate cancer.

reaction suitability

core: iron
reagent type: catalyst

Purification Methods

It crystallises as yellow crystals from pet ether (m 225-230odec), CHCl3 (m 208.5odec), toluene/pet ether (m 195-205odec), or aqueous ethanol. [Matsue et al. J Am Chem Soc 107 3411 1985.] The acid chloride m 49o crystallises from pentane, and has max at 458nm [Lau & Hart J Org Chem 24 280 1959]. The methyl ester crystallises from aqueous MeOH with m 70-71o. The anhydride has m 143-145o when recrystallised from pet ether [Acton & Silverstein J Org Chem 24 1487 1959]. The amide has m 168-170o when crystallised from CHCl3/Et2O or m 167-169o when crystallised from *C6H6/MeOH. [Arimoto & Haven J Am Chem Soc 77 6295 1955, Benkeser et al. J Am Chem Soc 76 4025 1954.] [Beilstein 16 IV 1807.]

References

[1] C. Pessa, L. Kubota, Y. Gushikem. “Ferrocenecarboxylic acid adsorbed on Nb2O5 film grafted on a SiO2 surface: NADH oxidation study.” Electrochimica Acta 46 1 (2001): 2499–2505.
[2] H. Tsukube, S. Shinoda, H. Fukui. “Synergistic binding and chirality sensing of unprotected amino acids with ferrocenecarboxylic acid–crown ether conjugate.” Tetrahedron Letters 42 1 (2001): 7583–7585.

Ferrocenecarboxylic acid(1271-42-7)Related Product Information

• Folic acid
• tert-Butylferrocene
• Stearic acid
• Aminoferrocene
• ETHYNYLFERROCENE
• Ferrocene
• Hyaluronic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Ferrocenecarboxaldehyde
• Acetylferrocene
• Ferrocenemethanol
• Ferrocenecarboxamide
• Citric acid
• Ascoric Acid
• Ethylboronic acid
• 7-Bromo-2,4-dichloropyrido[3,2-d]pyrimidine
• 2-HYDROXYTHIOPHENOL
• 3-Amino-6-methylpicolinic acid