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Acetylferrocene is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 1271-55-2 Structure
  • Basic information

    1. Product Name: Acetylferrocene
    2. Synonyms: Ferrocenyl methyl ketone, 99+%;Iron, (acetylcyclopentadienyl)cyclopentadienyl-;Acetylferrocene,95%;Acetylferrocene ,98%;NSC 115511;ACETYLFERROCENE FOR SYNTHESIS;1-Ferrocenylethanone;ACETYLFERROCENE
    3. CAS NO:1271-55-2
    4. Molecular Formula: C12H12FeO
    5. Molecular Weight: 228.07
    6. EINECS: 215-043-2
    7. Product Categories: Ferrocene series;metallocene;1,2,4-Triazole,Triazoles;Industrial/Fine Chemicals
    8. Mol File: 1271-55-2.mol
  • Chemical Properties

    1. Melting Point: 81-83 °C(lit.)
    2. Boiling Point: 160-163 °C (3.0004 mmHg)
    3. Flash Point: 160-163°C/4mm
    4. Appearance: Orange/Needle-Like Crystalline Powder
    5. Density: >1 g/cm3 (20℃)
    6. Vapor Pressure: 1.77mmHg at 25°C
    7. Refractive Index: 1.502
    8. Storage Temp.: Store below +30°C.
    9. Solubility: N/A
    10. Water Solubility: insoluble
    11. Stability: Stable. Incompatible with strong oxidizing agents, reducing agents, strong acids, strong bases.
    12. CAS DataBase Reference: Acetylferrocene(CAS DataBase Reference)
    13. NIST Chemistry Reference: Acetylferrocene(1271-55-2)
    14. EPA Substance Registry System: Acetylferrocene(1271-55-2)
  • Safety Data

    1. Hazard Codes: T+
    2. Statements: 28
    3. Safety Statements: 28-36/37-45-28A-1
    4. RIDADR: UN 2811 6.1/PG 2
    5. WGK Germany: 3
    6. RTECS: OB3700000
    7. F: 10
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: II
    11. Hazardous Substances Data: 1271-55-2(Hazardous Substances Data)

1271-55-2 Usage

Chemical Properties

orange crystalline powder

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.

Safety Profile

Poison by ocular and intravenous routes. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Orange-red crystals are obtained when it is recrystallised from isooctane or *C6H6, and then sublimed at 100o/1mm. The oxime has m 167-170o (from Et2O or aqueous EtOH). The semicarbazone has m 198-201o (from EtOH). [Richmond & Freiser J Am Chem Soc 77 2022 1955, Weinmayer J Am Chem Soc 77 3009 1955, Broadhead et al. J Chem Soc 650 1958, Beilstein 16 IV 1798.]

Check Digit Verification of cas no

The CAS Registry Mumber 1271-55-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,7 and 1 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1271-55:
(6*1)+(5*2)+(4*7)+(3*1)+(2*5)+(1*5)=62
62 % 10 = 2
So 1271-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O/c1-6(8)7-4-2-3-5-7/h2-5,7H,1H3

1271-55-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A13078)  1-Acetylferrocene, 97%   

  • 1271-55-2

  • 5g

  • 253.0CNY

  • Detail
  • Alfa Aesar

  • (A13078)  1-Acetylferrocene, 97%   

  • 1271-55-2

  • 25g

  • 854.0CNY

  • Detail
  • Alfa Aesar

  • (A13078)  1-Acetylferrocene, 97%   

  • 1271-55-2

  • 100g

  • 2871.0CNY

  • Detail
  • Alfa Aesar

  • (A13078)  1-Acetylferrocene, 97%   

  • 1271-55-2

  • 250g

  • 6102.0CNY

  • Detail
  • Aldrich

  • (106860)  Acetylferrocene  95%

  • 1271-55-2

  • 106860-5G

  • 355.68CNY

  • Detail
  • Aldrich

  • (106860)  Acetylferrocene  95%

  • 1271-55-2

  • 106860-25G

  • 1,009.71CNY

  • Detail

1271-55-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Acetylferrocene

1.2 Other means of identification

Product number -
Other names ferrocenyl methyl ketone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1271-55-2 SDS

1271-55-2Related news

The preparation of (5-aryl-3-isoxazolyl)-ferrocenes from dilithiated Acetylferrocene (cas 1271-55-2) oxime and aromatic esters08/18/2019

Acetylferrocene oxime was dilithiated with excess lithium diisopropylamide and the resulting C(α),O-dilithiated oxime was condensed at the carbanion-type center with aromatic esters to yield C-acylated intermediates that were quenched and acid-cyclined to the (5-aryl-3-isoxazolyl)-ferrocenes (i...detailed

Synthesis and structures of Acetylferrocene (cas 1271-55-2) thiosemicarbazones and their dimethylthallium(III) complexes, which have four- or five-membered chelate rings08/17/2019

Five thiosemicarbazones HLn=Fc(Me)C(2)N(3)N(2)(H)C(1)(S)N(1)R1R2 (Fc=ferrocenyl) were prepared by condensing acetylferrocene with thiosemicarbazide or 4-substituted thiosemicarbazides: acetylferrocene thiosemicarbazone (HL1), acetylferrocene 1N-methylthiosemicarbazone (HL2), acetylferroc...detailed

Chelates of Acetylferrocene (cas 1271-55-2) benzoylhydrazone with lanthanides08/15/2019

The chelates, Ln(HL)2Cl3·nH2O of acetylferrocene benzoylhydrazone with 15 lanthanide(III) metals have been prepared and characterized by elemental analysis, IR, UV, molar conductance, TG and DTA. It was found that the ligand coordinates to the central ions in the keto form, and some chloride io...detailed

Evaluation of diesel fuel-biodiesel blends with palladium and Acetylferrocene (cas 1271-55-2) based additives in a diesel engine08/11/2019

Influence of biodiesel-diesel fuel blends with acetylferrocene and palladium based additives on diesel engine performance and emissions were studied experimentally. The additives were dosed into the blend fuels as 25 ppm. Bis-[N,N-dimethyl-N′-2-chlorobenzoylthioureato] palladium (II), PdL2 was ...detailed

Highly selective synthesis of Acetylferrocene (cas 1271-55-2) by acylation of ferrocene over zeolites08/10/2019

Zeolites with different structure and concentration of acid sites were investigated in a liquid phase acylation of ferrocene with acetic anhydride. It was found that the conversion of ferrocene increased in the order: medium pore zeolitesdetailed

Solubilities of ferrocene and Acetylferrocene (cas 1271-55-2) in supercritical carbon dioxide08/09/2019

In this work, the solubilities of ferrocene and acetylferrocene in supercritical carbon dioxide (scCO2) were measured using an analytical method in a quasi-flow apparatus. High-performance liquid chromatography was applied through an online sampling procedure to determine the concentration of fe...detailed

1271-55-2Relevant articles and documents

Metal complexation of thioacylferrocenes: crystal structures of pentacarbonyl(thiobenzoylferrocene-S)chromium and benzoylferrocene

Barnes, John C.,Bell, William,Glidewell, Christopher,Howie, R. Alan

, p. 369 - 378 (1990)

Acylferrocenes (C5H5)Fe(C5H4COR) (R=CH3, C2H5, (CH3)2CH, (CH3)3C or Ph) can be readily thionated to give thioacylferrocenes by use of P4S10 in non-polar solvents such as CH2Cl2 or toluene; use of polar solvents such as THF or diglyme provides very poor conversions.Thiobenzoylferrocene reacts readily with Et4N+-- (M = Cr, Mo, or W) in the presence of silver nitrate to yield (C5H5)Fe>, in which the M(CO)5 group is bonded to the sulphur atom as revealed by an X-ray diffraction study.The structure consists of isolated molecules in which a Cr(CO)5 fragment of approximate C4v symmetry is bonded via sulphur to the thioacylferrocene with an Cr-S bond length of 2.412(1) Angstroem, an S=C bond length of 1.667(2) Angstroem and a C-S-Cr angle of 121.9(1) deg.Photo oxidation of (C5H5)Fe> yields benzoylferrocene the crystal structure of which was determined.

Improvement of ferrocene acylation. Conventional vs. microwave heating for scandium-catalyzed reaction in alkylmethylimidazolium-based ionic liquids

Berardi, Serena,Conte, Valeria,Fiorani, Giulia,Floris, Barbara,Galloni, Pierluca

, p. 3015 - 3020 (2008)

Acylation of ferrocene-catalyzed by scandium triflate was thoroughly investigated. Reaction time and temperature are important parameters, in that prolonged treatment causes substrate decomposition and/or catalyst deactivation. Hydrophobic alkylmethylimid

Generation of ferrocenylvinyl cation CpFeC5H4–C+=CH2 by protonation of ferrocenylacetylene with Nafion and its reactions with SMe2 and PPh3 in scCO2 giving onium salts

Kizas, Ol'ga A.,Chaschin, Ivan S.,Godovikov, Ivan A.,Dolgushin, Fedor M.,Antonov, Dmitrii Yu.,Nikitin, Lev N.,Khokhlov, Alexei R.

, p. 368 - 370 (2017)

Cation CpFeC5H4–C+=CH2 was obtained by protonation of FcC[tbnd6]CH with Nafion superacid in DMF or scCO2 and characterized by NMR spectroscopy. The protonation in the presence of SMe2 or PP

The synthesis of ferrocenyl- and ferrocenoylpyrimidines

Zherebker,Rodionov,Pilipenko,Kachala,Nikitin,Belousova,Simenel

, (2014)

New derivatives of pyrimidine were synthesized from ferrocenyl ketones by the reactions of [3+1+1+1]annulation and intermolecular cyclization. The electrochemical behavior of the obtained compounds was studied by the method of cyclic voltammetry. All the

Palladium-Catalyzed Removable 8-Aminoquinoline Assisted Chemo- and Regioselective Oxidative sp2-C-H/sp3-C-H Cross-Coupling of Ferrocene with Toluene Derivatives

Sattar, Moh.,Kumar, Sangit

, p. 5960 - 5963 (2017)

The coupling of the C(sp2)-H bond of ferrocene with toluene avoiding in situ functionalization of both coupling partners has been achieved using palladium and iron dual catalysis. This cross oxidative coupling features regioselectivity to prima

Fabrication of bisferrocenyl derivative grafted HTPB with high iron content and its application in dopamine detection

Aghaiepour, Alireza,Rahimpour, Shabnam,Payami, Elmira,Mohammadi, Reza,Teimuri-Mofrad, Reza

, (2021)

In this work, we employed an efficient strategy to increase the graft percentage of ferrocene in hydroxyl terminated polybutadiene (HTPB) polymer framework. For this purpose, we use 5-chloro-2-pentanone to attach the two alkylferrocene derivatives to each other. In order to incorporate the obtained bis-alkylferrocene derivatives to the polymer backbone, the chlorine atom at the end of the coupling agent alkyl chain was converted to a silane group using the Grignard reaction. Finally, hydrosilylation reaction of as-synthesized silane derivatives and HTPB in the presence of Speier's catalyst (H2PtCl6) resulted in novel bis-ferrocene modified HTPBs with a variety of iron contents. The iron percentage, viscosity, and glass transition temperature of the novel bis-ferrocene modified HTPBs as essential parameters of polymer characterization were investigated. Obtained polymers are electro-active due to the presence of ferrocenyl groups. Additionally, unlike the virgin polymer (HTPB) they show optical properties. The final polymer was immobilized onto the bare glassy carbon electrode (GCE) surface using the cross-linking effect of terephthaldehyde (TFA) and fresh egg white (FEW). Electrochemical impedance spectroscopy (EIS) confirmed the successful immobilization of the polymer. The ability of the fabricated electrode to mediate dopamine (DA) oxidation was evaluated, and the results show the acceptable detection limits as well as linear ranges for the determination of dopamine using GC/BEFcHTPB/(TFA+FEW).

Very high rate enhancement of benzyl alcohol oxidation by an artificial enzyme

Marinescu, Lavinia G.,Bols, Mikael

, p. 4590 - 4593 (2006)

(Figure Presented) Promoting the atomic dialogue! At neutral pH and ambient temperature, a cyclodextrin-derived ketone causes hydrogen peroxide and benzyl alcohols to meet in its active site and react up to 60 000 times faster than they do outside the cyclodextrin.

Tuneable superbase-catalyzed vinylation of α-hydroxyalkylferrocenes with alkynes

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.

, p. 5954 - 5960 (2014)

Superbase-catalyzed (KOH/DMSO suspension as a catalyst) vinylation of hydroxymethyl- and hydroxyethylferrocenes with terminal and internal alkynes (acetylene, propyne, phenylacetylene, 3-ethynylpyridine, 1-propyn-1-yl-benzene, diphenylacetylene) affords hitherto unknown vinyl ethers of ferrocene in 30-93% yields depending on the alkyne structure and the tuneable ratio of reactants/KOH/DMSO. The vinylation smoothly proceeds under mild conditions (70-90 °C, 0.25-13 h). With unsubstituted acetylene the process is readily realized under atmospheric pressure (yield of the corresponding vinyl ethers is 81-90%) though under pressure (initial pressure at room temperature is 10-13 atm, maximum pressure is 13-16 atm at the reaction temperature) the yield is close to quantitative (93%). The synthesized compounds were characterized using 1H and 13C NMR, and IR spectroscopy, as well as X-ray diffraction analysis.

Synthesis, characterization and electrochemical properties of novel trinuclear ferrocenyl based organosilane compounds

Teimuri-Mofrad, Reza,Safa, Kazem D.,Rahimpour, Keshvar

, p. 36 - 44 (2014)

Some trinuclear ferrocenyl based organosilane compounds were synthesized by hydrosilylation reaction of [4-(ethylferrocenyl)butyl]dimethylsilane and (4-ferrocenylbutyl)dimethylsilane with bisalkenylferrocene derivatives, in the presence of the Karstedt catalyst at room temperature. In addition a simple method for the preparation of 1,1′-bis(3-butenyl)alkylferrocenes from 1,1′-bis(4-chlorobutyl)alkylferrocenes under mild conditions was developed. 1H and 13C NMR, FT-IR, GC-MS, CHN analysis, atomic absorbtion spectroscopy supported the predicted structure of the products. The electrochemical behavior of synthesized compounds was studied by cyclic voltammetry in CH3CN/0.1 M LiClO4 utilizing a glasse carbon working electrode. The relationship between the peak currents and the square root of the scan rate, showed that the redox process is diffusion limited.

Assembly of dendrimers with redox-active [{CpFe(μ3-CO)} 4] clusters at the periphery and their application to oxo-anion and adenosine-5′-triphosphate sensing

Aranzaes, Jaime Ruiz,Belin, Colette,Astruc, Didier

, p. 132 - 136 (2006)

9, 16, or 27 [CpFe(μ3-CO)]4 clusters contain the title assemblies (see picture). The one-electron oxidation Fe 4→Fe4+of all Fe4 units appears as a single reversible cyclic voltammetry wave and was used in solution and with dendrimer-modified electrodes for oxo-anion recognition. ATP2- is selectively recognized and better than H2PO4-. The larger the dendrimer, the easier is the re-use of the modified electrode sensor. (Chemical Equation Presented)

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