1271-48-3

Usage

Uses

Used in Chemical Synthesis:
1,1'-Ferrocenedicarboxaldehyde is used as a starting material for the preparation of various ferrocene derivatives, such as 1'-formyl-ferrocenecarboxylic acid and 1'-[(E)-3-oxo-but-1-enyl]-ferrocenecarboxylic acid. These compounds are synthesized through oxidation reactions with potassium permanganate using water/acetonitrile mixture and water/acetone mixture, respectively. The resulting products have potential applications in the development of new materials and catalysts.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1,1'-Ferrocenedicarboxaldehyde and its derivatives could potentially be used in the pharmaceutical industry for the development of novel drugs, given their unique chemical properties and reactivity.
Used in Material Science:
The unique properties of 1,1'-Ferrocenedicarboxaldehyde and its derivatives may also find applications in material science, particularly in the development of new materials with specific electronic, magnetic, or catalytic properties.

Upstream product

• 102-54-5 ferrocene 
• 93-61-8 N-methyl-N-phenylformamide 
• 68-12-2 N,N-dimethyl-formamide 
• 1293-65-8 1,1'-dibromoferrocene 
• 2591-86-8 N-Formylpiperidine 
• 1461-22-9 tributyltin chloride 
• 12093-10-6 ferrocenecarboxaldehyde 
• 1287-13-4 bis(η⁵-cyclopentadienyl)ruthenium 

Downstream Products

• 1291-47-0 1,1'-dimethylferrocene 
• 916906-88-2 cyclohexyl 1,1'-bisferrocenylimine 
• 947280-85-5 N,N'-(ferrocene-1,1'-diyldimethylylidene)di(4-bromoaniline) 
• 947280-84-4 N,N'-(ferrocene-1,1'-diyldimethylylidene)di(4-chloroaniline) 
• 1211094-56-2 Fe(C₅H₄CHC₅H₂O(C₆H₅)2)(C₅H₄CHO) 

Relevant academic research and scientific papers

Synthesis, characterization and third-order nonlinear optical properties of symmetrical ferrocenyl Schiff base materials

Six symmetrical ferrocenyl Schiff base materials were synthesized and characterized by UV, 1H NMR, mass spectrometry (MS) and elemental analysis. Their off-resonant third-order nonlinear optical properties were measured using femtosecond laser

The highly regiospecific synthesis and crystal structure determination of 1,1′-2,5′ substituted ring-locked ferrocenes

1,1′-Ferrocene biscarboxaldehyde (1) has been prepared and the aldehyde groups were subsequently protected with acetal groups to produce 1,1′-bisacetalferrocene (2). A ring-locked ferrocene was synthesised by further derivatisation of the cyclopentadiene

An improved synthesis of ferrocene-1,1'-dicarbaldehyde

Ferrocene-1,1'-dicarbaldehyde has been prepared in 70percent yield in a one-pot procedure from dilithioferrocene-TMEDA complex and dimethylformamide.

Preparation, characterization and electrochemical and X-ray structural studies of new conjugated 1,1′-ferrocenediyl-ended [CpFe-arylhydrazone] + salts

A series of new conjugated bimetallic ferrocenyl 1,1′-bis- substituted compounds of the type (E)-[CpFe(η6-p-RC 6H4)NHN=CH(η5-C5H 4)Fe(η5-C5H4)-CH=CHC 6H4-p-R′]+PF6- (Cp = η5-C5H5; R, R′ = H, NO 2, 11; Me, NO2, 12; MeO, NO2, 13; Cl, NO 2, 14; Me, CN, 15; Me, Me, 16), with end-capped (E)-ethenylaryl and [CpFe(arylhydrazone)]+ substituents, have been prepared by the condensation reaction of 1,1′-(p-R′-arylethenyl) ferrocenecarboxaldehyde (R′ = Me, 4; NO2, 5; CN, 6) with the organometallic hydrazine precursors [CpFe(η6-p-RC 6H4NHNH2)]+PF6 - (R = H, 7; Me, 8; MeO, 9; Cl, 10). In the trimetallic series, {[CpFe(η6-p-RC6H4)NHN=CH(η 5-C5H4)]2Fe}2+[PF 6-]2 (R = H, 17; Me, 18; MeO, 19, Cl, 20), which results from the condensation of two equivalents of the same organometallic hydrazine precursor (7-10) with 1,1′- ferrocenedicarboxaldehyde, the ferrocenediyl core symmetrically links two cationic mixed-sandwich units. These ten hydrazones (11-20) were stereoselectively obtained as their trans isomers about the N=C double bond. All the new compounds were thoroughly characterized by a combination of elemental analysis, spectroscopic techniques (1H NMR, IR and UV-Vis) and electrochemical studies in order to prove electronic interaction between the donating and accepting units through the π-conjugated system. A representative example of each series has also been characterized by single crystal X-ray diffraction analysis. The bimetallic complex 16+ adopts an anti conformation with the two iron atoms on opposite faces of the dinucleating hydrazonato ligand, whereas the trinuclear complex 192+ adopts a syn conformation with an Fe-Fe-Fe angle of 180°. Other salient features of these structures are the long Fe-Cipso bond distances and the slight cyclohexadienyl character at the coordinated C6 ring, with a folding angle of 7.4° and 7.0° for 16+ and 19 2+, respectively.

A new synthesis and electrochemistry of 1,1′-bis(β-hydroxyethyl)ferrocene

The preparation of 1,1′-bis(β-hydroxyethyl)ferrocene (1) by oxidation of 1,1′-divinylferrocene is described. Compound 1 has been characterized by 1H and 13C{1H} NMR, and cyclic voltammetry. The electrochemical data are com

A New Class of C2-Symmetric Chiral Cyclopentadienyl Ligand Derived from Ferrocene Scaffold: Design, Synthesis and Application

A new class of C2-symmetric, chiral cyclopentadienyl ligand based on planar chiral ferrocene backbone was developed. A series of its corresponding rhodium(I), iridium(I), and ruthenium(II) complexes were prepared as well. In addition, the rhodium(I) complexes were evaluated in the asymmetric catalytic intramolecular amidoarylation of olefin-tethered benzamides via C?H activation.

New Polyaza Tris-ferrocene and Tris-2,2'-bipyridyl Macrobicyclic Cryptand Molecules. Isolation of Homo- and Hetero-polymetallic Zinc(II) and Copper(I) Cryptates containing Externally Coordinated Ruthenium(II) Cations

New multisite ligands containing either three peripherally linked ferrocene redox centres (L1,L3) or three externally orientated 2,2'-bipyridyl transition metal recognition sites (L2,L4) have been prepared and t

Structural influences on the electrochemistry of 1,10-di(hydroxyalkyl) ferrocenes. Structure of [Fe{h5-C5H4eCH(OH)e(CH2)3OH}2]

Abstract A series of 1,1'-di(hydroxyalkyl)ferrocenes, [Fc'{(CH 2)nOH}2], with n = 1 (1), 2 (2), 3 (3) and 4 (4) and Fc' = Fe(η5-C5H4)2, was synthesized. The electrochemistry of the di(hydroxyalkyl)ferrocenes was studied by cyclic voltammetry in CH2Cl2/0.1 M [N nBu4][PF6] utilizing a glassy carbon working electrode. The ferrocenyl group showed reversible electrochemistry with the formal reduction potential, Eo' , inversely proportional to alkyl chain length and approximately 59 mV smaller than those of the corresponding mono(hydroxyalkyl)ferrocenes derivatives [Fc(CH2)mOH] with m = 1 (1m), 2 (2m), 3 (3m), and 4 (4m) and Fc = Fe(η5-C 5H5)(η5-C5H4 -). The tetraalcohol [Fc'{CH(OH)(CH2)3OH} 2], 5, possessing four OH functionalities, two in the terminal positions and two more, one on each of the two α-C relative to the ferrocenyl (Fc' for dialcohols or Fc for monosubstituted derivatives) group, was isolated as a side product during the synthesis of 4. The formal reduction potential of 5 was Eo' = -24 mV vs. FcH/FcH+ and closely approached Eo' of [FcCH(OH)CH3] (Eo' = -11 mV), [Fc'{CH(OH)CH3}2] (-21 mV) and 1 (0.00 mV vs. FcH/ FcH+). The single crystal X-ray structure of the tetraalcohol 5 (Z = 8, orthorhombic, space group Pbca) was also solved.

An Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction: Highly Efficient Method to Prepare Planar Chiral Ferrocenes

A Pd-catalyzed, asymmetric oxidative cross-coupling reaction between ferrocenes and heteroarenes is described. The process, which takes place via a twofold C-H bond activation pathway, proceeds with modest to high efficiencies (36-86%) and high levels of regio- and enantioselectivity (95-99% ee). In the reaction, air oxygen serves as a green oxidant and excess amounts of the coupling partners are not required. The process is the first example of a catalytic asymmetric biaryl coupling reaction that occurs via double C-H bond activation. Finally, the generated coupling products can be readily transformed into chiral ligands and catalysts.

Synthesis, molecular structure and properties of a ferrocene-based difluoropyrrolo-oxaborole derivative

Reaction of 1,1′-ferrocenedicarbonyl chloride with 3-ethyl-2,4-dimethylpyrrole in DCM produced the half-way product, namely, the ferrocene bis(2-ketopyrrole) derivative 2 and not the expected bis(dipyrromethene) compound. The 2-ketopyrrole compound readily reacted with BF3·Et2O to produce the bis(difluoropyrrolo)-oxaborole compound, FBF, as a red/brown solid which was characterised by X-ray crystallography. 57Fe M?ssbauer spectra for 2 and FBF were consistent with low-spin iron(II) (d6) ferrocene derivatives. A cyclic voltammogram for 2 in acetonitrile revealed a reversible wave at +0.31 V vs. Fc+/Fc (ferrocene-based) and an irreversible wave at -2.38 V vs. Fc+/Fc (ketopyrrole-based). The electrochemical behaviour is severely perturbed by the chelation of the BF2 groups. Alterations to the electronic properties of 2 by formation of FBF are also evident in the absorption profiles. DFT calculations [B3PW91, 6-31G(3df)] support the observed changes in the electrochemistry findings and the M?ssbauer spectroscopic data. Reaction of 1,1′-ferrocenedicarbonyl chloride with 3-ethyl-2,4-dimethylpyrrole produces the bis(ketopyrrole) compound. Chelation of BF2 to the ketopyrrole units forms the difluoropyrrolo-oxaborole.