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Acetylferrocene

Catalog Number: BT-257160

CAS Number: 1271-55-2

Molecular Formula: C12H4FeO-8

Molecular Weight: 228.07 g/mol

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Product Introduction

Description

Acetylferrocene is a derivative of ferrocene, a metallocene compound consisting of two cyclopentadienyl rings bound to a central iron atom. Acetylferrocene is synthesized by the acetylation of ferrocene, which involves the addition of an acetyl group to one of the cyclopentadienyl rings. Acetylferrocene has been extensively studied due to its unique chemical and biological properties.

Properties

CAS Number

1271-55-2

Product Name

Acetylferrocene

IUPAC Name

cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-ylethanone;iron(2+)

Molecular Formula

C12H4FeO-8

Molecular Weight

228.07 g/mol

InChI

InChI=1S/C7H3O.C5H.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h1H3;1H;/q2*-5;+2

InChI Key

SPKJCVZOZISLEI-UHFFFAOYSA-N

SMILES

CC(=O)[C-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.[Fe+2]

Solubility

Soluble in DMSO

Synonyms

1-Acetylferrocene; 1 Acetylferrocene; 1Acetylferrocene; Acetoferrocene; Acetylferrocene;

Canonical SMILES

CC(=O)[C-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.[Fe+2]

Isomeric SMILES

CC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]

Method of Synthesis or Extraction

Acetylferrocene can be synthesized by several methods, including Friedel-Crafts acylation, acetylation using acetic anhydride, and acetylation using acetyl chloride. The Friedel-Crafts acylation method involves the reaction of ferrocene with acetyl chloride in the presence of a Lewis acid catalyst, such as aluminum chloride. The acetylation using acetic anhydride method involves the reaction of ferrocene with acetic anhydride in the presence of a Lewis acid catalyst, such as sulfuric acid. The acetylation using acetyl chloride method involves the reaction of ferrocene with acetyl chloride in the presence of a base, such as pyridine. The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. The Friedel-Crafts acylation method is the most commonly used method for the synthesis of acetylferrocene, with a yield of up to 80%. However, this method requires the use of toxic and corrosive reagents, and the reaction conditions must be carefully controlled to prevent side reactions. The acetylation using acetic anhydride method is less efficient, with a yield of up to 50%, but it is safer and easier to perform. The acetylation using acetyl chloride method is also less efficient, with a yield of up to 60%, but it is less toxic than the Friedel-Crafts acylation method.

Chemical Structure and Biological Activity

The chemical structure of acetylferrocene consists of a ferrocene core with an acetyl group attached to one of the cyclopentadienyl rings. The acetyl group is a polar functional group that can interact with biological molecules, such as enzymes and receptors. Acetylferrocene has been shown to exhibit a wide range of biological activities, including anti-inflammatory, antioxidant, and anticancer properties. The mechanism of action of acetylferrocene is not fully understood, but it is believed to involve the modulation of cell signaling pathways and the inhibition of key enzymes involved in inflammation and cancer.

Biological Effects

Acetylferrocene has been shown to have a variety of effects on cell function and signal transduction. It has been shown to inhibit the production of pro-inflammatory cytokines, such as interleukin-1β and tumor necrosis factor-α, and to reduce the activation of nuclear factor-κB, a key transcription factor involved in inflammation. Acetylferrocene has also been shown to induce apoptosis, or programmed cell death, in cancer cells by activating the caspase cascade and inhibiting the anti-apoptotic protein Bcl-2. However, acetylferrocene can also have potential toxic effects, such as hepatotoxicity and nephrotoxicity, at high doses.

Applications

Acetylferrocene has potential applications in medical research, environmental research, and industrial research. In medical research, acetylferrocene has been studied for its role in drug development, particularly as a potential anticancer agent. Clinical trials have shown promising results in the treatment of various types of cancer, including breast cancer, lung cancer, and leukemia. However, further studies are needed to determine the optimal dosage and administration route, as well as the potential side effects. In environmental research, acetylferrocene has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have potential applications in the removal of heavy metals from contaminated soil and water. In industrial research, acetylferrocene has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account when handling acetylferrocene, as it is a potentially hazardous substance.

Future Perspectives and Challenges

Despite the promising results of studies on acetylferrocene, there are still several limitations in its use and study. One of the main challenges is the lack of understanding of its mechanism of action and its potential side effects. Further studies are needed to elucidate the molecular pathways involved in its biological activity and to determine the optimal dosage and administration route. Another challenge is the development of more efficient and environmentally friendly methods of synthesis. Possible solutions include the use of renewable resources and the development of catalysts that are less toxic and more selective. In the future, acetylferrocene has the potential to be used in a wide range of scientific research applications, including drug development, environmental remediation, and industrial manufacturing.

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