ACETYLFERROCENE

Acetylferrocene is a functional ferrocene derivative that combines the characteristic organometallic structure of ferrocene with a reactive acetyl substituent, making it a useful starting material for the preparation of more complex organometallic and aromatic compounds.
Acetylferrocene is frequently employed in synthetic chemistry, electrochemical studies, catalyst development, ligand preparation, and materials research, where its predictable redox behavior and accessible carbonyl functionality support a broad range of chemical transformations.
Acetylferrocene is also valuable in the development of redox-active molecules, specialty intermediates, sensors, coordination compounds, and functional materials that benefit from the electronic properties and structural versatility of the ferrocene framework.

CAS Number: 1271-55-2
EC Number: 215-043-2
Molecular Formula: C12H12FeO
Molecular Weight: 228.07 g/mol

Synonyms: RefChem:914995, DTXCID701783260, DTXSID101014560, 215-043-2, 1-Acetylferrocene, 1271-55-2, Acetylferrocene, Ferrocenyl methyl ketone, Ketone, ferrocenyl methyl, Monoacetylferrocene, Acetylferrocen, NSC20889, NSC-20889, STK332040, AKOS005439476, A0775, Acetylferrocen, [German], [IUPAC name – generated by ACD/Name], Acetylferrocene, [IUPAC name – generated by ACD/Name], Acétylferrocène, [French], [IUPAC name – generated by ACD/Name], Ferrocene, acetyl-, [Index name – generated by ACD/Name], Unverified, (2-acetylcyclopenta-2,4-dien-1-yl)(cyclopenta-2,4-dien-1-yl)iron, (Acetylcyclopentadienyl)cyclopentadienyliron, 1-Acetylferrocene, 1271-55-2, [RN], 215-043-2, [EINECS], Ferrocenyl methyl ketone, MFCD00001432, [MDL number]

Acetylferrocene is an organometallic compound consisting of a ferrocene core with an acetyl group.
The addition of the acetyl moiety enhances solubility and facilitates chemical modifications. 

Acetylferrocene's unique properties, including moderate thermal stability and reactivity, enable its use as an intermediate in synthesizing polymers and hybrid materials.
Acetylferrocene's application in organic electronics allows for improved charge transport and stability in electronic devices.

Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COCH3).
Acetylferrocene consists of ferrocene substituted by an acetyl group on one of the cyclopentadienyl rings.
Acetylferrocene is an orange, air-stable solid that is soluble in organic solvents.

Acetylferrocene is an organometallic compound that can be used as a catalyst and as a starting material for the synthesis of complex organometallic compounds.
Acetylferrocene is an organometallic compound derived from ferrocene in which one hydrogen atom of a cyclopentadienyl ring is replaced by an acetyl group.

Acetylferrocene is widely used as an intermediate and reference compound in organometallic chemistry, Friedel–Crafts acylation studies, and the synthesis of substituted ferrocene derivatives.
Acetylferrocene's combination of a ferrocene framework and a reactive carbonyl group makes Acetylferrocene useful in research involving coordination chemistry, electrochemistry, functional materials, and fine-chemical synthesis.

Acetylferrocene is an organometallic compound featuring a ferrocene backbone with an acetyl group.
Acetylferrocene provides a versatile intermediate for synthesizing various organometallic and polymeric materials, supporting advancements in electronic and material sciences.

Uses of Acetylferrocene:
Acetylferrocene was originally used in military or space field as an additive in rocket propellant, to promote the burning rate.
Acetylferrocene's ferrocenyl derivative has wide applications to biological and medical fields such as ferrocene-modified beta-lactam because of its physiological activity of anti-malarial, anti-tumor, bactericidal, anti-inflammatory, treatment of anemia, inhibition of enzymatic activity and so on by virtue of its unique structure and diverse properties.

Acetylferrocene is used as an intermediate in the synthesis of substituted ferrocene derivatives and other organometallic compounds.
Acetylferrocene is widely employed in academic and industrial research involving Friedel–Crafts acylation, organometallic reaction mechanisms, and coordination chemistry.

Acetylferrocene is used in electrochemical studies because the ferrocene framework provides characteristic and well-defined redox behavior.
Acetylferrocene serves as a starting material for the preparation of ligands, catalysts, and functional organometallic molecules.

Acetylferrocene is also investigated in materials chemistry for the development of redox-active compounds, sensors, and advanced functional materials.
Acetylferrocene's reactive carbonyl group enables further transformations such as reduction, condensation, and derivatization in fine-chemical synthesis.

Acetylferrocene can be used as:
A Precursor to synthesize 1-ferrocenylethanol by reduction in the presence of sodium borohydride.
An electroactive compound along with MgO nanoparticles to modify carbon paste electrode (CPE) that can be used to determine L-cysteine.

Chemical Synthesis:
Utilized as an intermediate in organic synthesis to develop various functionalized ferrocene derivatives, enabling enhanced properties for targeted applications.
Serves as a key ligand in coordination chemistry to synthesize metal complexes for catalysis, providing improved reactivity and selectivity for desired chemical transformations.

Materials Science:
Applied in the formulation of conductive polymers to enhance electrical properties, leading to optimized performance in electronic devices.
Ideal for use as a dopant in organic semiconductors, enhancing charge transport efficiency in organic photovoltaic cells.

Preparation and Reactions of Acetylferrocene:

Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac2O):
Fe(C5H5)2 + Ac2O → (C5H5)Fe(C5H4Ac) + HOAc

The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations.

Acetylferrocene can be converted to many derivatives, e.g., reduction to the chiral alcohol (C5H5)Fe(C5H4CH(OH)Me) and precursor to vinylferrocene.
The oxidized derivative, acetylferrocenium, is used as a 1e-oxidant in the research laboratory.

Preparation:
Acetylferrocene synthesis: Charge a 25 mL round bottom flask with ferrocene (1 g) and acetic anhydride (3.3 mL).
Carefully add phosphoric acid (0.7 mL, 85%) and heat the reaction mixture on a hot water bath for 20 min with stirring.

Pour the hot mixture onto crushed ice (27 g).
After all the ice has melted, neutralise the solution with solid sodium bicarbonate and cool for a further 5 min.

Collect the brown precipitate by filtration, wash with water and dry in the air.
The solid obtained is a mixture of unreacted ferrocene and the monosubstituted product acetylferrocene.
However, a third compound may also be present in very small amounts as the disubstituted product of acetylation (1,1′-diacetylferrocene).

Stability and Reactivity of Acetylferrocene:

Chemical stability:
Acetylferrocene is generally stable under normal ambient temperatures and recommended storage conditions.

Reactivity:
Acetylferrocene may react with strong oxidizing agents and other highly reactive materials.

Conditions to avoid:
Avoid excessive heat, ignition sources, dust formation, and prolonged exposure to incompatible substances.

Incompatible materials:
Keep away from strong oxidizing agents and other reactive chemicals.

Handling and Storage of Acetylferrocene:

Safe handling:
Handle with adequate ventilation and avoid inhalation of dust and unnecessary contact with the skin and eyes.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place.

First Aid Measures of Acetylferrocene:

Inhalation:
Move the affected person to fresh air and obtain medical attention if symptoms occur.

Skin contact:
Remove contaminated clothing and wash the affected area thoroughly with plenty of water.

Eye contact:
Rinse immediately with plenty of water for at least several minutes and obtain medical attention.

Ingestion:
Rinse the mouth and obtain medical attention promptly.

Firefighting Measures of Acetylferrocene:

Suitable extinguishing media:
Use dry chemical, carbon dioxide, water spray, or suitable foam according to surrounding fire conditions.

Protective equipment:
Firefighters should wear appropriate protective clothing and self-contained breathing apparatus.

Accidental Release Measures of Acetylferrocene:

Personal precautions:
Provide adequate ventilation, avoid dust formation, and prevent unnecessary contact with the spilled material.

Cleanup methods:
Carefully sweep or collect the material and transfer it into a suitable closed container for disposal.

Environmental precautions:
Prevent unnecessary release into drains, waterways, and the surrounding environment.

Exposure Controls/Personal Protective of Acetylferrocene:

Engineering controls:
Provide adequate general or local exhaust ventilation and ensure suitable washing facilities are available.

Eye protection:
Wear appropriate safety glasses or chemical goggles.

Hand protection:
Wear suitable protective gloves.

Skin protection:
Wear appropriate protective clothing.

Respiratory protection:
Use suitable respiratory protection when ventilation is inadequate or significant dust exposure may occur.

Identifiers of Acetylferrocene:
CAS No.: 1271-55-2
Chemical Name: Acetylferrocene
CBNumber: CB3165427
Molecular Formula: C12H12FeO10*
Molecular Weight: 228.07
MDL Number: MFCD00001432

CAS Number: 1271-55-2
ChemSpider: 21241939
ECHA InfoCard: 100.013.676
EC Number: 215-043-2
PubChem CID: 10857189
RTECS number: OB3700000
InChI: InChI=1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-5H,1H3;1-5H;
Key: PHMAOJNZIFULOG-UHFFFAOYSA-N
SMILES: CC(=O)[C]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe]

Product Number: A0775
Purity / Analysis Method: >98.0%(GC)
Molecular Formula / Molecular Weight: C12H12FeO = 228.07
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 1271-55-2
Reaxys Registry Number: 3947753
PubChem Substance ID: 125308257
SDBS (AIST Spectral DB): 7071
MDL Number: MFCD00001432

Empirical Formula (Hill Notation): C12H12FeO
CAS Number: 1271-55-2
Molecular Weight: 228.07
NACRES: NA.22
PubChem Substance ID: 24846743
UNSPSC Code: 12161600
EC Number: 215-043-2
MDL Number: MFCD00001432

Properties of Acetylferrocene:
Assay: 95%
Form: solid
InChI Key: PHMAOJNZIFULOG-UHFFFAOYSA-N
InChI: 1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-5H,1H3;1-5H;
Melting Point: 81-83 °C (lit.)
Quality Level: 100
Reaction Suitability: core: iridium, reagent type: catalyst
SMILES String: [Fe].[CH]1[CH][CH][CH][CH]1.CC(=O)[C]2[CH][CH][CH][CH]2

Chemical Formula: [Fe(C5H4COCH3)(C5H5)]
Molar Mass: 228.07 g/mol
Appearance: Red brown crystal
Density: 1.014 g/mL
Melting Point: 81 to 83 °C (178 to 181 °F; 354 to 356 K)
Boiling Point: 161 to 163 °C (322 to 325 °F; 434 to 436 K) (4 mmHg)
Solubility in Water: Insoluble in water, soluble in most organic solvents

Melting Point: 81-83 °C (lit.)
Boiling Point: 160-163 °C (3.0004 mmHg)
Density: >1 g/cm3 (20℃)
Flash Point: 160-163°C/4mm
Storage Temperature: Sealed in dry,Room Temperature
Form: Needle-Like Crystalline Powder
Color: Orange
Water Solubility: insoluble
Exposure Limits: ACGIH: TWA 1 mg/m3
NIOSH: TWA 1 mg/m3
Stability: Stable. Incompatible with strong oxidizing agents, reducing agents, strong acids, strong bases.
InChI: InChI=1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-5H,1H3;1-5H;
InChIKey: PHMAOJNZIFULOG-UHFFFAOYSA-N
SMILES: [C]1(C(=O)C)[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: 1271-55-2(CAS DataBase Reference)
EWG's Food Scores: 1
NIST Chemistry Reference: Acetylferrocene(1271-55-2)
EPA Substance Registry System: Ferrocene, acetyl- (1271-55-2)
UNSPSC Code: 12161600
NACRES: NA.22

Molecular Weight: 228.07 g/mol
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 1
Exact Mass: 228.023751 Da
Monoisotopic Mass: 228.023751 Da
Topological Polar Surface Area: 17.1 Ų
Heavy Atom Count: 14
Complexity: 152
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

Product Name: Acetylferrocene, 95%
Quality Segment: 100
Assay: 95%
Form: solid
Reaction Suitability: core: iridium, reagent type: catalyst
Melting Point: 81-83 °C (lit.)
SMILES String: [Fe].[CH]1[CH][CH][CH][CH]1.CC(=O)[C]2[CH][CH][CH][CH]2
InChI: 1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-5H,1H3;1-5H;
InChI Key: PHMAOJNZIFULOG-UHFFFAOYSA-N

Specifications of Acetylferrocene:
Appearance: Orange to Amber to Dark red powder to crystal
Purity (GC): min. 98.0 %
Melting Point: 83.0 to 87.0 °C
NMR: confirm to structure

Names of Acetylferrocene:

IUPAC name:
1-Ferrocenylethan-1-one

Other name:
Acetylferrocene