1293-79-4

Usage

Uses

Used in Organometallic Synthesis:
Chlorocarbonyl ferrocene serves as a key building block in the synthesis of other organometallic compounds. Its presence in these compounds is crucial for achieving desired chemical properties and reactivity.
Used in Catalyst Preparation:
In the field of catalysis, chlorocarbonyl ferrocene is used in the preparation of organometallic catalysts. These catalysts are vital for facilitating various chemical reactions, enhancing the efficiency and selectivity of processes in organic synthesis.
Used in Organic Synthesis:
Chlorocarbonyl ferrocene has been investigated for its potential use in catalytic reactions, particularly within the realm of organic synthesis. Its versatility makes it a promising candidate for the development of novel synthetic pathways and the production of complex organic molecules.
Used in Material Development:
Chlorocarbonyl ferrocene's unique properties also lend themselves to the development of new materials. Researchers are exploring its potential applications in creating advanced materials with specific characteristics for use in various industries.
Used in Pharmaceutical Research:
Due to its reactivity and the ability to form complexes, chlorocarbonyl ferrocene is also being studied for its potential applications in pharmaceutical research. It may contribute to the discovery of new drug candidates or the improvement of drug delivery systems.

Upstream product

• 1271-42-7 ferrocenecarboxylic acid 
• 10026-13-8 phosphorus pentachloride 
• 7719-12-2 phosphorus trichloride 
• 7719-09-7 thionyl chloride 
• 102-54-5 ferrocene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 12093-10-6 ferrocenecarboxaldehyde 
• 639-58-7 triphenyltin chloride 
• 88568-67-6 p-hydroxyphenyl ferrocenecarboxylate 
• 88568-66-5 1,4-bis(2-ferrocenecarboxylate)benzene 
• 165749-55-3 N,N'-bis[(3,4-dimethoxybenzo-1-yl)methyl]-N,N'-bis[ferroceneoxo]ethylenediamine 
• 220113-16-6 (((3-methylphenyl)amino)carbonyl)ferrocene 
• 403612-83-9 N-tert-butyl-N'-ferrocenoyl-N-benzoylhydrazine 
• 403612-85-1 N-tert-butyl-N-ferrocenoyl-N'-benzoylhydrazine 
• 403612-86-2 ClC₆H₄CONHN(C(CH₃)3)COC₅H₄FeC₅H₅ 
• 403612-84-0 N-tert-butyl-N'-ferrocenoyl-N-(3,5-dimethyl)benzoylhydrazine 
• 554-68-7 triethylamine hydrochloride 
• 108037-18-9 ((C₅H₅)Fe)2(C₅H₄CH(P(C₆H₅)3)COC₅H₄)⁽¹⁺⁾*I^(1-)=[((C₅H₅)Fe)2(C₅H₄CH(P(C₆H₅)3)COC₅H₄)]I 
• 779339-34-3 2,6-dimethyl-4-tert-butylphenyl ferrocenoyl selenide 
• 779339-35-4 phenyl ferrocenoyl selenide 

Relevant academic research and scientific papers

1,2-DISUBSTITUIERTE FERROCENE VIA 2-FERROCENYL-2-OXAZOLINE

2-Ferrocenyl-2-oxazolines, available from the reaction of chlorocarbonylferrocene with aziridines and subsequent acid-catalyzed isomerisation, are metallated (lithiated) regiospecifically in the 2-position of the ferrocenyl moiety.Further reaction of the metallated compounds with electrophiles gives 1,2-disubstituted ferrocenes solely.In contrast to the analogous 2-phenyl-2-oxazolines, 2-ferrocenyl-2-oxazolines exhibit high stability under acid-catalyzed solvolytic attack conditions.The reason for this unexpected behaviour is discussed.

Asymmetric synthesis of planar chiral ferrocenes by enantioselective intramolecular C-H arylation of N-(2-haloaryl)ferrocenecarboxamides

The palladium-catalyzed intramolecular C-H arylation reaction of N-(2-bromoaryl)ferrocenecarboxamides furnishes planar chiral ferrocene derivatives. TADDOL-derived phosphoramide ligands induce enantioselectivities ranging from 91:9 to 98:2 er. (Chemical Equation Presented).

Palladium-Catalyzed C-H Functionalization of Ferrocenecarboxylic Acid by using 8-Aminoquinoline as a Removable Directing Group

A mild and efficient palladium-catalyzed synthetic method for the C-H functionalization of N-(quinolin-8-yl)ferrocenecarboxamide has been developed. Various aryl iodides containing I, NO2, CN, COMe, CO2Et, and NH functionalities and also alkyl iodides underwent the Pd-catalyzed intermolecular carbon-carbon bond forming reaction with ferrocenecarboxamide successfully which led to a diverse array of bis(aryl/alkyl)ferrocenecarboxamides in 34-92% yields. Cross-coupling of the ferrocenyl C-H bond with aryl iodides can also be achieved utilizing an economical Ni catalyst. Additionally, selective monoalkylation of ferrocenecarboxamide was studied using sodium bicarbonate as base and dibenzylphosphoric acid as additive under Pd-catalyzed reaction conditions. Subsequently, removal of the directing group, 8-aminoquinoline, from bis(aryl)ferrocenecarboxamides led to bis(aryl)ferrocenes bearing versatile methyl ester and carboxaldehyde functional groups.

Electrochemical Assay for Extremely Selective Recognition of Fructose Based on 4-Ferrocene-Phenylboronic Acid Probe and β-Cyclodextrins Supramolecular Complex

The aim of the present paper is to highlight a novel electrochemical assay for an extremely-selective detection of fructose thanks to the use of a supramolecular complex between β-cyclodextrins (β-CDs) and a chemically modified ferrocene with boronic acid named 4-Fc-PB/natural-β-CDs. Another kind of β-CDs, the 4-Fc-PB/3-phenylboronic-β-CDs, is proposed for the detection of glucose. The novel electrochemical probe is fully characterized by 1H nuclear magnetic resonance, mass spectroscopy, and elemental analysis, while the superior electrochemical performance is assessed in terms of sensitivity and detection limit. The novelty of the present work consists in the role of CDs that for the first time are employed in electrochemistry with a unique detection mechanism based on specific chemical interactions with the target molecule by the introduction of proper binding groups. A?highly selective detection of fructose is obtained and it is believed that the proposed mechanism of detection represents a new way to electrochemically sense other molecules by varying the combination of specific groups of the supramolecular complex. The findings are of impactful importance since a quick, easy, cheap, and extremely selective detection of fructose is not yet available in the market, here achieved by using electrochemical methods which are a very growing field.

Functionalized ferrocenes: The role of the para substituent on the phenoxy pendant group

Six ferrocenecarboxylates with phenyl, 4-(1H-pyrrol-1-yl)phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl as pendant groups were synthesized and fully characterized by spectroscopic, electrochemical and X-ray diffraction methods. The anti-proliferative activity of these complexes were investigated in hormone dependent MCF-7 breast cancer and MCF-10A normal breast cell lines, to determine the role of the para substituent on the phenoxy pendant group. The 4-fluorophenyl ferrocenecarboxylate is inactive in both cell lines while 4-(1H-pyrrol-1-yl)phenyl ferrocenecarboxylate is highly cytotoxic in both cell lines. 4-chlorophenyl and 4-bromophenyl ferrocenecarboxylates have moderate to good anti-proliferative activity in MCF-7 and low anti-proliferative activity on normal breast cell line, MCF-10A whereas the 4-iodophenyl analog is highly toxic on normal breast cell line. The phenyl ferrocenecarboxylate has proliferative effects on MCF-7 and is inactive in MCF-10A. Docking studies between the complexes and the alpha-estrogen receptor (ERα) were performed to search for key interactions which may explain the anti-proliferative activity of 4-bromophenyl ferrocenecarboxylate. Docking studies suggest the anti-proliferative activity of these ferrocenecarboxylates is attributed to the cytotoxic effects of the ferrocene group and not to anti-estrogenic effects.

Synthesis, characterization and electrical conductance of ferrocenylazobenzene

Ferrocenylazobenzene was synthesized by condensing an aminoazobenzene dye with ferrocenecarboxylic acid previously treated with oxalyl chloride. The compound displayed an anticipated chemically reversible one-electron oxidation process and gave a formal potential, E° = 0.65 V. In the UV-Vis region, the azo π-π and n-π transitions appeared at 355 and 460 nm respectively. On oxidation of the ferrocenyl moiety, the azo π-π band was blue-shifted to 348 nm with an increase in intensity, while a new broad, lower energy absorption band assigned to the ligand-to-metal charge transfer appeared at 622 nm. The growth of this new band was concurrent with the bleaching of the metal-to-ligand charge transfer band which was largely obscured by the azo n-π band at 460 nm. The compound in the form of thin film gave an average electrical conductivity of 0.239 ± 0.001 Scm-1 and a non-linear I-V curve with knee voltage at 2.3 V in dark condition.

N-Cobaltocenium Amide as Reactive Nucleophilic Reagent for Donor-Acceptor Bimetallocenes

Deprotonation of the aminocobaltocenium ion [Cc-NH2]+ ([H-1]+) generates the nucleophilic imine CcNH (1). Reaction of 1 with acid chlorides R-COCl (R = Ph, Fc, and Cc+) yields the reference amide [Ph-CO-NH-Cc]+ (2+) and the amide-linked hetero- and homobimetallocenes [Fc-CO-NH-Cc]+ (3+) and [Cc-CO-NH-Cc]2+ (42+), respectively. Cation-anion interactions of charged amides 2+-42+ in the solid state and in solution are probed by single crystal X-ray diffraction and NMR and IR spectroscopy. Intramolecular metal-metal interactions in donor-acceptor heterobimetallocene 3+ and in mixed-valent homobimetallocene 4+ (prepared electrochemically) are discussed within the Marcus-Hush framework aided by spectroelectrochemical experiments and time-dependent density functional theory calculations.

Synthesis of Chiral-Substituted 2-Aryl-ferrocenes by the Catellani Reaction

A palladium-catalyzed and norbornene-mediated methodology has been developed for the synthesis of chiral 2-aryl-ferroceneamides from chiral 2-iodo-N,N-diisopropylferrocencarboxamide, iodoarenes, and alkenes using a JohnPhos ligand and potassium carbonate as a base in dimethylformamide at 105 °C. The developed three-component coupling protocol allows the compatibility of electron-withdrawing fluoro, chloro, ester, and nitro and electron-donating methyl, methoxy, dimethoxy, benzyl ether-substituted iodo-benzenes, other iodoarenes, such as iodo-naphthalene, heteroarenes, such as iodothiophene, and terminating substrates, such as methyl, ethyl, tert-butyl acrylates, and substituted styrenes with 2-iodo-N,N-diisopropylferrocencarboxamide. Furthermore, the developed three-component Catellani method proceeded with the retention of the configuration of the planar chiral ferrocene, which depends on the role of the participating carbon-iodine bond in ferrocene. Consequently, the developed protocol enabled the formation of densely substituted chiral 2-aryl ferroceneamides, exhibiting good to excellent enantioselectivity. The conversion of an ester of the synthesized chiral 2-aryl ferroceneamides has also been carried out to further accommodate the easily expendable acid and alcohol functionalities.

Self-assembled bio-organometallic nanocatalysts for highly enantioselective direct aldol reactions

Supramolecular nanocatalysts were designed for asymmetric reactions through the self-assembly process of a bio-organometallic molecule, ferrocene-L-prolinamide (Fc-CO-NH-P). Fc-CO-NH-P could self-assemble into versatile nanostructures in water, including nanospheres, nanosheets, nanoflowers, and pieces. In particular, the self-assembled nanoflowers exhibited a superior specific surface area, high stability, and delicate three-dimensional (3D) chiral catalytic active sites. The nanoflowers could serve as heterogeneous catalysts with an excellent catalytic performance toward direct aldol reactions in aqueous solution, achieving both high yield (>99%) and stereoselectivity (anti/syn = 97:3, ee% >99%). This study proposed a significant strategy to fabricate supramolecular chiral catalysts, serving as a favorable template for designing new asymmetric catalysts.

Ferrocene derivatives of liquid chiral molecules allow assignment of absolute configuration by X-ray crystallography

The present study investigates a synthetically simple ferrocene derivatization of natural products and active pharmaceutical ingredients. Seven new crystal structures are analyzed together with 16 structures of ferrocene derivatives reported previously. In all cases, the unambiguous determination of the absolute structure was established from anomalous dispersion using the methods of Flack and Parsons. A comparison with other derivatization approaches shows the advantage of the described ferrocene derivatization for establishing the absolute configuration of novel compounds.