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1271-55-2

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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

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  • (Code)Product description
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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.

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

Patin, H.

, (1974)

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.

Hall, D. W.,Richards, J. H.

, p. 1549 - 1554 (1963)

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)

Synthesis of new binuclear ferrocenyl compounds by hydrosilylation reactions

Teimuri-Mofrad, Reza,Mirzaei, Farzaneh,Abbasi, Hassan,D. Safa, Kazem

, p. 197 - 205 (2017)

Ferrocenyl silanes are prepared by treatment of Grignard reagents produced from 4-chlorobutylferrocene derivatives and chlorodimethylsilane in THF. Butenylferrocenes are prepared by the elimination reaction of 4-chlorobutylalkylferrocenes by sodium tert-butoxide in DMSO. A hydrosilylation reaction between a butenyl compound and ferrocenylsilane occurred in dry toluene at room temperature in the presence of the Karstedt catalyst to produce the desired binuclear ferrocenyl compound in good to high yields. The electrochemical behavior of new ferrocenyl compounds were studied by cyclic voltammetry in CH3CN/0.1?M LiClO4, and the relation between the peak currents and the square root of the scan rate, showed that the redox process is diffusion-limited.

Hauser, C. R.,Lindsay, J. K.

, p. 482 - 485 (1957)

The d4/d3 redox pairs [MX(CO)(η-RCCR)Tp′] z (z = 0 and 1): Structural consequences of electron transfer and implications for the inverse halide order

Adams, Christopher J.,Bartlett, Ian M.,Carlton, Susannah,Connelly, Neil G.,Harding, David J.,Hayward, Owen D.,Orpen, A. Guy,Patron, Elena,Ray, Christopher D.,Rieger, Philip H.

, p. 62 - 72 (2007)

The d4 halide complexes [MX(CO)(η-RCCR)Tp′] {X = F, Cl, Br or I; R = Me or Ph; M = Mo or W; Tp′ = hydrotris(3,5- dimethylpyrazolyl)borate} undergo one-electron oxidation to the d3 monocations [MX(CO)(η-RCCR)Tp′]+, isolable for M = W, R = Me. X-Ray structural studies on the redox pairs [WX(CO)(η-MeCCMe)Tp′] z (X = Cl and Br, z = 0 and 1), the ESR spectra of the cations [WX(CO)(η-RCCR)Tp′]+ (X = F, Cl, Br or I; R = Me or Ph), and DFT calculations on [WX(CO)(η-MeCCMe)Tp′]z (X = F, Cl, Br and I; z = 0 and 1) are consistent with electron removal from a HOMO (of the d4 complexes) which is π-antibonding with respect to the W-X bond, π-bonding with respect to the W-C(O) bond, and δ-bonding with respect to the W-Calkyne bonds. The dependence of both oxidation potential and ν(CO) for [MX(CO)(η-RCCR)Tp′] shows an inverse halide order which is consistent with an ionic component to the M-X bond; the small size of fluorine and its closeness to the metal centre leads to the highest energy HOMO and the lowest oxidation potential. In the cations [MX(CO)(η-RCCR)Tp′] + electronegativity effects become more important, leading to a conventional order for Cl, Br and I. However, high M-F π-donation is still facilitated by the short M-F distance. The Royal Society of Chemistry.

Buell, G. R.,McEwen, W. E.,Kleinberg, J.

, p. 40 - 43 (1962)

1-Ethyl-3-methylimidazolium halogenoaluminate melts as reaction media for the Friedel-Crafts acylation of ferrocene

Surette, Jacqueline K. D.,Green, Laine,Singer, Robert D.

, p. 2753 - 2754 (1996)

Ionic liquid mediated Friedel-Crafts acylation of the organometallic complex ferrocene can be performed in 1-ethyl-3-methylimidazolium halogenoaluminate melts, EtMeimI-AlCl3, as well as in the liquid clathrate formed upon addition of an excess

Synthesis and thermal performance of poly(cyclotriphosphazene- acetylferrocene) derivative

Zhao, Zhengping,Yu, Fengying

, p. 3639 - 3642 (2014)

Amino nucleophilic reagents were prepared by using acetylferrocene and diamines and then the iron-phosphazene derivative was first synthesized by the nucleophilic substitution reaction of hexachlorocyclotriphosphazene and the amino nucleophilic reagent. FT-IR curve proved that the aim product was synthesized and the chlorine atom of iron-phosphazene derivative did not completely replaced. The thermal performance of the iron-phosphazene derivative was examined by TGA. This suggests that the iron-phosphazene derivative began to degrade at 200 °C and still has 25 % residue at 700 °C. The residues morphology of the iron-phosphazene derivative was also examined. The surface of residues was smooth, fibrous arrangement and has a certain orientation structure. EDS confirmed that the main components of the higherature calcined residues were C, P and Fe.

Ferrocenylalkylation of 2-mercaptobenzoxazoles

Osipova, E. Yu.,Ivanova,Rodionov,Korlyukov,Arkhipov,Simenel

, (2016)

Regioselectivity of the HBF4-catalyzed ferrocenylalkylation of 2-mercaptobenzoxazole in two phase aqueous organic solvent mixture was studied. The reaction proceeds regioselectively at the heterocyclic nitrogen atom. Structures of the synthesiz

A simple synthetic approach for the transformation of (S)-Ugi's amine

Zha, Gao-Feng,Xu, Wei-Yun,Dai, Peng,Lai, Xiao-Yan,Liu, Wei,Shen, Yong-Cun

, p. 1301 - 1304 (2014)

A simple synthetic approach for the transformation of (S)-Ugi's amine, another configuration of (R)-Ugi's amine, one of the most widely used intermediate in the preparation of chiral ferrocene-based ligands, has been developed via esterification using anhydride, alkaline hydrolysis and active manganese dioxide oxidation, and the corresponding ferrocenyl ketone was afforded in good yields.

Novel meso-substituted ferrocene-appended porphyrins: Synthesis, characterization, and electrochemical evaluation

Payami, Elmira,Neshad, Saeed,Aghaiepour, Alireza,Teimuri-Mofrad, Reza

, (2021/09/08)

This paper focuses on the synthesis of the novel ferrocene-appended porphyrin architectures and their zinc metal complexes. Tetraferrocenylporphyrins are a class of organometallic compounds where the porphyrin core is functionalized with a ferrocenyl unit at each of the four meso positions. Tetraferrocenylporphyrin derivatives were synthesized via a direct tetramerization reaction between some ferrocene carboxaldehyde derivatives and pyrrole in the presence of BF3·Et2O as an efficient catalyst. Moreover, a metalation reaction between tetraferrocenylporphyrin derivatives and zinc acetate was applied in the synthesis of related zinc complexes. The structures of the new organometallic compounds were confirmed by Fourier transform infrared spectroscopy (FT-IR), 1H NMR, 13C NMR, UV–vis, and CHNS analyses. The redox-active properties of the synthesized compounds were characterized by cyclic voltammetry (CV) analysis.

Cu2+-selective naked-eye ‘off–on' fluorescent probe with multisignals: chromaticity, fluorescence, electrochemistry

Xu, Xiuling,Zhang, Xiaoli,Cao, Cuilan,Zheng, Bingbing,Deng, Hongxia,Shuai, Qi

, p. 1142 - 1150 (2020/05/25)

In this study, a rhodamine–acetylferrocene conjugate of RBFc was synthesized and then characterized using spectroscopy and single-crystal analysis. The chemosensor RBFc exhibited a marked colour change from colourless to pink after binding to Cu2+ ions. Importantly, under the presence of the other competing cations in aqueous solution, only Cu2+ ions caused spirolactam ring opening in rhodamine B in RBFc, resulting in an enhanced absorbance of ultraviolet light spectra and fluorescence spectra, as well as obvious shifts in cyclic voltammetry curves and differential pulsed voltammetry curves. The novel probe described in this manuscript provides an attractive approach for detecting Cu2+ in the presence of other multisignals.

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