1,1'-Ferrocenedicarboxaldehyde

Base Information

• Chemical Name: 1,1'-Ferrocenedicarboxaldehyde
• CAS No.: 1271-48-3
• Molecular Formula: C12H10FeO2
• Molecular Weight: 242.057
• Hs Code.: 29319090
• Mol file: 1271-48-3.mol

Synonyms:1,1'-Diformylferrocene;Ferrocene-1,1'-biscarboxaldoxime;Ferrocene-1,1'-dicarbaldehyde;1,1'-Ferrocenedicarboxaldehyde(8CI);1,1'-Bisformylferrocene;

Chemical Property of 1,1'-Ferrocenedicarboxaldehyde

Chemical Property:

• Appearance/Colour: yellow-orange
• Melting Point: 151-156 °C(lit.)
• PSA: 34.14000
• LogP: 1.17870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

1,1′-Ferrocenedicarboxaldehyde 96% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 1,1'-Ferrocenedicarboxaldehyde (FcDa) is a versatile ferrocene derivative with two aldehyde functional groups at the 1,1' positions, making it useful as a cross-linking agent and precursor for Schiff base formation. It exhibits reducibility due to the Fe(II) center, enabling in situ reduction of Ag⁺ to Ag nanoparticles (AgNPs) in chitosan films, leading to plasmonic color-switching properties and antimicrobial activity. Additionally, FcDa serves as a key intermediate in synthesizing symmetrical ferrocenyl Schiff bases and conjugated bimetallic/tri-metallic complexes, demonstrating electrochemical interactions and structural versatility in coordination chemistry. Its applications span smart materials, nonlinear optics, and antimicrobial films.

Technology Process of 1,1'-Ferrocenedicarboxaldehyde

There total 10 articles about 1,1'-Ferrocenedicarboxaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

ferrocene (102-54-5,55404-68-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ferrocenecarboxaldehyde (12093-10-6) + 1,1'-ferrocenyldicarboxaldehyde (1271-48-3)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; n-heptane; under N2; tBuLi in hexane is added to ferrocene in THF at -20°C, stirred for 30 min, DMF is added at -10°C, HCl is added; extd. with CH2Cl2, chromd. (SiO2, CH2Cl2);

DOI:10.1016/0022-328X(93)83414-Q

Reference yield: 88.0%

ferrocene (102-54-5,55404-68-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 1,1'-ferrocenyldicarboxaldehyde (1271-48-3)

Guidance literature:

ferrocene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; at -78 - 20 ℃; for 20.1667h; Inert atmosphere; Schlenk technique;

N,N-dimethyl-formamide; In diethyl ether; hexane; at -78 ℃; for 1.66667h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.202001814

Reference yield: 80.0%

N-Formylpiperidine (2591-86-8) + ferrocene (102-54-5,55404-68-7) → 1,1'-ferrocenyldicarboxaldehyde (1271-48-3)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; Ar; ferrocene (53.8 mmol) suspnd. in hexane, hexane soln. of BuLi (107.5mmol) added, TMEDA (55.7 mmol) added dropwise, stirred at room temp. fo r 14 h, Et2O soln. of ligand (104.1 mmol) added dropwise, stirred for 30min; extd. (H2O), reextd. (CH2Cl2), org. layer washed (aq. HCl), dried (MgSO4), filtered, concd., chromd. (SiO2, CH2Cl2/hexane=1/1), dried;

DOI:10.1016/j.ica.2008.09.017

upstream raw materials:

ferrocene

N,N-dimethyl-formamide

bis(η⁵-cyclopentadienyl)ruthenium

ferrocenecarboxaldehyde

Downstream raw materials:

1,1'-bis[4-[bis(pentachlorophenyl)methyl]-2,3,5,6-tetrachlorostyryl]ferrocene

Fe(C₅H₄CHC₅H₂O(C₆H₅)2)(C₅H₄CHO)