1272-44-2

Usage

Uses

Used as an Intermediate:
Benzoylferrocene serves as an intermediate in the synthesis of various organic compounds, making it a valuable building block in organic chemistry.
Used in Deprotonative Metalation of Ferrocenes:
It is used as a reactant in the deprotonative metalation of ferrocenes, which is a key step in the synthesis of various ferrocenyl compounds.
Used in Oxidative Chemistry:
Benzoylferrocene is utilized in oxidative chemistry, where it can act as a reducing agent or participate in redox reactions.
Used in Reduction of Ferrocenyl Ketones:
It is employed as a reactant for the reduction of ferrocenyl ketones, which is an important reaction in the synthesis of ferrocenyl alcohols and other related compounds.
Used in Polymerization of C-Ferrocenyl-Substituted Phosphaalkene:
Benzoylferrocene is used in the polymerization of C-ferrocenyl-substituted phosphaalkenes, contributing to the development of new materials with unique properties.
Used as a Reactant for Synthesis:
Benzoylferrocene is used as a reactant in the synthesis of various compounds, such as planar chiral triferrocenylmethane derivatives and chiral ferrocenyl alcohols via asymmetric transfer hydrogenation.

Hazard

Possibly toxic.

InChI:InChI=1/C12H10O/c13-12(11-8-4-5-9-11)10-6-2-1-3-7-10/h1-9,11H

Upstream product

• 15321-51-4 diiron nonacarbonyl 
• 102-54-5 ferrocene 
• 85-44-9 phthalic anhydride 
• 703-59-3 homophthalic anhydride 
• 613-94-5 benzoic acid hydrazide 
• 104067-61-0 phenyl ferrocenyl ketimine hydrochloride 
• 7681-65-4 copper(l) iodide 
• 98-88-4 benzoyl chloride 
• 1274-09-5 bis(ferrocenyl)mercury 
• 1271-15-4 lithiumferrocene 
• 100-47-0 benzonitrile 
• 100-52-7 benzaldehyde 
• 15617-18-2 bis(benzonitrile)palladium(II) dichloride 

Downstream Products

• 102-54-5 ferrocene 
• 14900-04-0 triiodide^(1-) 

Related news

Synthesis and characterization of novel heteroannular Benzoylferrocene (cas 1272-44-2) polysiloxane monomers, oligomers, and polymers08/11/2019

Copoly[2,2′-bis[1,1′-ferrocene]benzoylylene/3,3,5,5-tetramethyl-4-oxa-3,5-disila-1,7-heptanylene] (III) was synthesized by two approaches. High molecular weight III was obtained by an acid catalyzed equilibrium condensation of 1,1′-bis[1-(3′,3′,5′,5′-tetramethyl-4-oxa-3,5-disilahexyl)benz...detailed

Syntheses, third-order optical nonlinearity and DFT studies on Benzoylferrocene (cas 1272-44-2) derivatives08/09/2019

A series of benzoylferrocene derivatives were synthesized and their third-order nonlinear optical (NLO) properties were evaluated in N,N-dimethyl-formamide at 800 nm using femtosecond degenerate four-wave mixing. The third-order NLO susceptibilities of synthesized compounds were 3.065–7.859 × ...detailed

Relevant academic research and scientific papers

REACTION OF METALLOCENYL THIOKETONES WITH C5H5- AND - ANIONS. PREPARATION AND CRYSTAL STRUCTURES OF DIMERIC CYMANTRENYLPHENYLFULVENE DERIVATIVES

Ferrocenyl- and cymantrenyl-phenylthioketone react with C5H5- or - anions forming ferrocenyl- and cymantrenyl-phenylfulvene.The latter readily undergoes a Diels-Alder dimerization or a cycloaddition with a starting thioketone or analogous ketone.Crystal structures of two dimeric products were established.

Structural features of lithio[3]ferrocenophane systems bearing stabilizing dimethylamino substituents

Treatment of the a-dimethylamino[3]ferrocenophane derivative 3 with n-butyllithium results in a directed o-metalation at the adjacent Cp ring of the ferrocene unit to selectively yield the (R*,R*,p-S*) diastereomer 4. Similarly, lithiation of rac-12 gives (R*,p-S*)-13. Both these compounds form mesc-type dimers in the crystal that feature a central C2Li2 four-membered-ring moiety. Compound 13 crystallizes with excess n-butyllithium to form a (13-n-BuLi) dimer that was also characterized by X-ray diffraction. Directed lithiation of the nonbridged ferrocene derivative l-(dimethylaminobenzyl)ferrocene (16) with tertbutyllithium resulted in an opposite stereoselectivity to yield (R*,p-R*)-17, which forms a chiral dimeric structure in the solid state, as was revealed by its X-ray crystal structure analysis.

FRIEDEL-CRAFTS ALKYLATIONS OF FERROCENE WITH UNSATURATED LACTONES, SOME UNUSUAL REACTIONS CAUSED BY THE Β-FERROCENYLCARBENIUM ION

Friedel-Crafts alkylations of ferrocene with 5- and 6-membered unsaturated lactones have been studied.The expected alkylation products were isolated in the case of 5-membered lactones, while several products such as unsaturated ferrocenyllactones, ferrocenyldiketones as well as ferrocenylhydroxylactones were isolated in the case of 6-membered lactones. β-Ferrocenylcarbenium ion was suggested to be the key intermediate in this case.

Synthesis of ferrocenyl thioketones and their reactions with diphenyldiazomethane

A series of ferrocenyl ketones were obtained via the Friedel-Crafts acylation with mixed anhydrides using ferrocene as a nucleophilic agent or ferrocene carboxylic acid as a precursor of the electrophilic species. The ketones obtained thereby undergo smooth thionation (tetrahydrofuran, 65°C) with Lawesson's reagent. The ferrocenyl thioketones react with diphenyldiazomethane via N2 elimination to afford the hitherto unknown ferrocenyl-substituted thiiranes.

Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes

Alkylidene carbenes undergo rapid inter- and intramolecular reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of 13C-labeled precursors. Herein we report on the rearrangement of 13C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [13C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (13C{1H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally.

Diastereoselective Double C?H Functionalization of Chiral Ferrocenes with Heteroaromatics

Diastereoselective double C?H heteroarylation of chiral ferrocenes provides valuable compounds with multiple functionalities using mild reaction conditions and simple reagents. Pd-Complexes with chiral mono-protected amino acids afforded corresponding heteroarylated ferrocenyl amines in good yields and high diastereomeric purities. In this way, a variety of indole, thiophene, pyrrole, or furan substituents were introduced to the ferrocene moiety. Furthermore, a range of relevant functional groups, for example ketone, ester, chloro, nitro, or silyl, are tolerated by this method. An alternative combination of amino acid and ferrocenyl amine configurations was leveraged to provide the complementary diastereomeric products. The products of C?H heteroarylation can be transformed into corresponding phosphines. Absolute configurations of CH-activation products were confirmed by the combination of X-ray crystallographic analysis and CD spectroscopy. 19F NMR kinetic study and DFT calculations provided insights into the reaction mechanism and reasons governing stereoinduction.

Highly Enantioselective Cobalt-Catalyzed Hydroboration of Diaryl Ketones

A highly enantioselective cobalt-catalyzed hydroboration of diaryl ketones with pinacolborane was developed using chiral imidazole iminopyridine as a ligand to access chiral benzhydrols in good to excellent yields and ee. This protocol could be carried out in a gram scale under mild reaction conditions with good functional group tolerance. Chiral biologically active 3-substituted phthalide and (S)-neobenodine could be easily constructed through asymmetric hydroboration as a key step.

Impact of the α-Ferrocenyl Group on the Solvolytic Reactivity – Electrofugality – of Ferrocenylphenylmethyl Cations

The electron-donating effect of the ferrocenyl group in α-position to the reaction center on SN1 solvolytic reactivity has been quantified by determining the electrofugalities (Ef) of a series of ferrocenyl-X-phenylmethyl cations according to the LFER equation: log k = sf(Ef + Nf). Due to highly stabilized transition state, the Ef values are about eight units higher than those of the corresponding benzhydryl cations. Impact of the phenyl group in ferrocenylphenylmethyl derivatives on stabilization of the positive charge is somewhat leveled by the ferrocenyl group, so the rate effect of the substituents on the phenyl ring is suppressed, causing narrow range of Ef parameters and small absolute values of the ρ+ constant. Calculations at B2PLYP-D3/may-cc-pVTZ level of theory showed that the positive charge in ferrocenylphenylmethyl cation is largely shifted from the phenyl to ferrocenyl moiety, and that the substituents on the phenyl ring have small impact on its stability.

Design, synthesis and fungicidal activity studies of 3-ferrocenyl-N-acryloylmorpholine

Ferrocene and its derivatives have been widely used in many fields and also used to modify and improve the performance. Particularly, their low toxicity also attract much attention in medical and pesticide fields. In order to get fungicides with higher biological activity, ferrocenyl groups were introduced into the skeleton of dimethomorph instead of phenyl groups and a series of 3-ferrocenyl-N-acryloylmorpholine were synthesized. The fungicidal bioassay results indicated that most of compounds showed moderate fungicidal activities against 14 kinds of agricultural pathogenic fungi and some compounds displayed higher fungicidal activities than that of dimethomorph. Intrestlingly, compounds 5(Z) exhibited better fungicidal activity against Sclerotinia sclerotiorum than that of compound 5(E).

Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects

Ferrocenylalkyl nitro-imidazoles (4a-h, 5a-h) were prepared via the regiospecific reaction of the α-(hydroxy)alkyl ferrocenes, FcCHR (OH) (1a–h; Fc = ferrocenyl; R = H, Me, Et, Pr, i-Pr, Ph, ortho-Cl-Ph, ortho-I-Ph), with nitro-imidazoles in aqueous organic medium (H2O-CH2Cl2) at room temperature in the presence of HBF4, within several minutes in good yields. X-ray structural data for racemic (R,S)-1-N-(benzyl ferrocenyl)-2-methyl-4-nitroimidazole (5f) were determined. The resulting enantiomers were resolved into enantiomers by analytical HPLC on modified amylose or cellulose chiral stationary phases. The viabilities of 4b, 4d, 5b, 5c in vitro, and in experiments in vivo antitumor effects of 1-N-ferrocenylethyl-4-nitroimidazole (4b) against murine solid tumor system Ca755 carcinoma were evaluated.