Acetylferrocen

Base Information

• Chemical Name: Acetylferrocen
• CAS No.: 1271-55-2
• Molecular Formula: C12H12FeO
• Molecular Weight: 228.074
• Hs Code.: 29310095
• NSC Number: 20889
• Mol file: 1271-55-2.mol

Synonyms:Acetylferrocen;NSC20889;NSC-20889;STK332040;AKOS005439476;A0775

Chemical Property of Acetylferrocen

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 1.77mmHg at 25°C
• Melting Point: 81-86 ºC
• Refractive Index: 1.502
• Boiling Point: 218 ºC at 760 mmHg
• Flash Point: 99.1 ºC
• PSA: 17.07000
• Density: 1.014g/cm³
• LogP: 1.99970
• Storage Temp.: Store below +30°C.
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 228.023751
• Heavy Atom Count: 14
• Complexity: 152

Purity/Quality:

99.9% ^*data from raw suppliers

Acetylferrocene, 99.5% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45-28A-1

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC=C[CH-]1.[CH-]1C=CC=C1.[Fe+2]
• Uses: 1-Acetylferrocene was originally used in military or space field as an additive in rocket propellant, to promote the burning rate. Its 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.

Technology Process of Acetylferrocen

There total 105 articles about Acetylferrocen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

ferrocene (102-54-5,55404-68-7) + acetic anhydride (108-24-7) → acetylferrocene (1271-55-2)

Guidance literature:

With phosphoric acid; In water; at 0 ℃; for 0.25h; Reflux;

Reference yield: 97.0%

ferrocene (102-54-5,55404-68-7) + acetyl chloride (75-36-5) → acetylferrocene (1271-55-2)

Guidance literature:

With zinc(II) oxide; In dichloromethane; Reflux; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.5b01548

Reference yield: 95.0%

(S)-1-hydroxyethylferrocene → acetylferrocene (1271-55-2)

Guidance literature:

With manganese(IV) oxide; In toluene; at 20 ℃; for 4h; Solvent; Reagent/catalyst; Time;

DOI:10.1016/j.cclet.2014.06.009

upstream raw materials:

ferrocene

1,1-dichloroethane

Acetyl bromide

2-methylbenzene diazonium

Downstream raw materials:

1-ferrocenylethanol

ferrocenecarboxylic acid

hydrogenchloride

(C₅H₅)Fe(C₅H₄COCH₂C₆H₄CN)

Refernces

• 1、 Berardi, Serena,Conte, Valeria,Fiorani, Giulia,Floris, Barbara,Galloni, Pierluca. "Improvement of ferrocene acylation. Conventional vs. microwave heating for scandium-catalyzed reaction in alkylmethylimidazolium-based ionic liquids". . p. 3015 - 3020. Retrieved 2008.
• 2、 Rinehart, K. L.,Curby, R. J.,Sokol, P. E.. "". . p. 3420 - 3424. Retrieved 1957.
• 3、 Sattar, Moh.,Kumar, Sangit. "Palladium-Catalyzed Removable 8-Aminoquinoline Assisted Chemo- and Regioselective Oxidative sp2-C-H/sp3-C-H Cross-Coupling of Ferrocene with Toluene Derivatives". . p. 5960 - 5963. Retrieved 2017.
• 4、 Aghaiepour, Alireza,Rahimpour, Shabnam,Payami, Elmira,Mohammadi, Reza,Teimuri-Mofrad, Reza. "Fabrication of bisferrocenyl derivative grafted HTPB with high iron content and its application in dopamine detection". . . Retrieved 2021.
• 5、 Trofimov, Boris A.,Oparina, Ludmila A.,Tarasova, Olga A.,Artem'ev, Alexander V.,Kobychev, Vladimir B.,Gatilov, Yuriy V.,Albanov, Alexander I.,Gusarova, Nina K.. "Tuneable superbase-catalyzed vinylation of α-hydroxyalkylferrocenes with alkynes". . p. 5954 - 5960. Retrieved 2014.
• 6、 Teimuri-Mofrad, Reza,Safa, Kazem D.,Rahimpour, Keshvar. "Synthesis, characterization and electrochemical properties of novel trinuclear ferrocenyl based organosilane compounds". . p. 36 - 44. Retrieved 2014.
• 7、 Kadkin, Oleg N.,Kim, Eun Ho,Kim, So Yeon,Choi, Moon-Gun. "Synthesis and liquid crystal properties of copper(II) and palladium(II) chelates with new ferrocene-containing enaminoketones". . p. 1301 - 1307. Retrieved 2009.
• 8、 Paucar, Rocío,Martín-Escolano, Rubén,Moreno-Viguri, Elsa,Cirauqui, Nuria,Rodrigues, Carlos Rangel,Marín, Clotilde,Sánchez-Moreno, Manuel,Pérez-Silanes, Silvia,Ravera, Mauro,Gabano, Elisabetta. "A step towards development of promising trypanocidal agents: Synthesis, characterization and in vitro biological evaluation of ferrocenyl Mannich base-type derivatives". . p. 569 - 582. Retrieved 2019.
• 9、 Shi, Yao-Cheng,Shen, Wen-Bin,Yang, Hua-Mei,Song, Hai-Bin,Hu, Xiao-Ya. "Copper and nickel complexes of the tetradentate ligand derived from the condensation of ferrocenoylacetone with 1,2-diaminoethane". . p. 749 - 754. Retrieved 2004.
• 10、 Teimuri-mofrad, Reza,Safa, Kazem D.,Abedinpour, Saiedeh,Rahimpour, Keshvar. "Synthesis of 5-(dimethylsilyl)pentylalkylferrocene-grafted HTPB (alkylFc-HTPB) via platinum-catalyzed hydrosilylation". . p. 2177 - 2185. Retrieved 2017.