1272-44-2

Basic information

• Product Name: Benzoylferrocene
• Synonyms: benzoyl-ferrocen;Ferrecenophenone;Ferrocene, benzoyl-;Iron(II), (benzoylcyclopentadienyl)cyclopentadienyl-;Ketone, ferrocenyl phenyl;Methanone, ferrocenylphenyl-;Monobenzoylferrocene;FERROCENYL PHENYL KETONE
• CAS NO: 1272-44-2
• Molecular Formula: C₁₇H₁₄FeO
• Molecular Weight: 290.14
• EINECS: 215-054-2
• Product Categories: Industrial/Fine Chemicals;Pharmaceutical Intermediates;Classes of Metal Compounds;Fe (Iron) Compounds;Ferrocenes;Metallocenes;Transition Metal Compounds
• Mol File: 1272-44-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 105-107 °C(lit.)
• Boiling Point: 283.7°C at 760 mmHg
• Flash Point: 118.7°C
• Appearance: /solid
• Density: 1.117g/cm³
• Vapor Pressure: 0.00311mmHg at 25°C
• Refractive Index: 1.597
• Water Solubility: Insoluble in water
• CAS DataBase Reference: Benzoylferrocene(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoylferrocene(1272-44-2)
• EPA Substance Registry System: Benzoylferrocene(1272-44-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1272-44-2(Hazardous Substances Data)

Usage

Description

Benzoylferrocene is an organic compound that consists of a ferrocene core with a benzoyl group attached to it. It is a red to red-brown powder and is known for its unique chemical properties and potential applications in various fields.

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-) 
• 19229-76-6 iron(III) 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 501-58-6 bis(4-methoxyphenyl)diazene 

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 articles and documents

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.

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.

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.

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.