Ferrocene-2-carboxaldehyde

Base Information

• Chemical Name: Ferrocene-2-carboxaldehyde
• CAS No.: 12093-10-6
• Molecular Formula: C11H10FeO
• Molecular Weight: 214.047
• Hs Code.: 29319090
• Wikidata: Q30943857
• Mol file: 12093-10-6.mol

Synonyms:ferrocene-2-carboxaldehyde;F0998;Q30943857

Chemical Property of Ferrocene-2-carboxaldehyde

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 5.03mmHg at 25°C
• Melting Point: 118-120 °C(lit.)
• Refractive Index: 1.623
• Boiling Point: 213.6 °C at 760 mmHg
• Flash Point: 98.8 °C
• PSA: 17.07000
• Density: 1.149g/cm3
• LogP: 1.60960
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: INSOLUBLE
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 214.008100
• Heavy Atom Count: 13
• Complexity: 121

Purity/Quality:

99% ^*data from raw suppliers

Ferrocenecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [CH-]1C=CC=C1.[CH-]1C=CC=C1C=O.[Fe+2]
• General Description: Ferrocenecarboxaldehyde, also known as formylferrocene or ferrocenealdehyde, is a key precursor in the synthesis of planar chiral ferrocene-based ligands, particularly those featuring additional central and axial chirality. It serves as a crucial starting material for constructing highly tunable Schi? base ligands used in stereoselective homogeneous catalysis, including applications such as epoxide ring-opening, Diels–Alder reactions, and asymmetric copolymerization. Its reactivity allows for modular diastereoselective transformations, enabling the formation of tridentate and tetradentate ligand frameworks with controlled steric and electronic properties.

Technology Process of Ferrocene-2-carboxaldehyde

There total 147 articles about Ferrocene-2-carboxaldehyde 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: 98.0%

ferrocene (102-54-5,55404-68-7) + N-methyl-N-phenylformamide (93-61-8) → ferrocenecarboxaldehyde (12093-10-6)

Guidance literature:

N-methyl-N-phenylformamide; With trichlorophosphate; at 0 ℃; for 0.25h;

ferrocene; at 20 ℃; Inert atmosphere;

DOI:10.1039/c6tc03876j

Reference yield: 92.0%

1-ferrocenylmethanol (1273-86-5) → ferrocenecarboxaldehyde (12093-10-6)

Guidance literature:

With ferrocene-labeled Merrifield resin-supported ionic liquid ([FemDMMerA]RuO₄); In tetrahydrofuran; for 4h; Reflux; Green chemistry;

DOI:10.1007/s11164-016-2563-2

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

upstream raw materials:

1-ferrocenylmethanol

ferrocenyl-pentacarbonylmanganese

acetonitrile

ferrocenoyl-pentacarbonylmanganese

Downstream raw materials:

(1-ferrocenyl)imino-benzyldiethylphosphonate

1-ferrocenyl-2-phenylethylene

[α-(N,N-dibenzylamino)-γ-phenylpropynyl]ferrocene

[α-(N,N-diallylamino)-γ-phenylpropynyl]ferrocene

Refernces

Planar chiral ferrocene salen-type ligands featuring additional central and axial chirality

10.1016/j.jorganchem.2005.11.051

The research reports on the synthesis and characterization of novel chiral tridentate [NO2]H2 and tetradentate [N2O2]H2 Schi? base ligands containing a planar chiral ferrocene moiety linked to hydroxyl-imine or diimine donors with central or axial chirality. The purpose of this study is to develop a new family of highly chiral ligands for use in stereoselective homogeneous catalysis, particularly for applications such as epoxide ring-opening, Diels–Alder reactions, imine cyanation, conjugate addition, hydrogenation, and the stereoselective alternating copolymerization of carbon monoxide with propylene oxide. The modular synthesis involves diastereoselective metalation of chiral ferrocene or pentamethylferrocene acetals, followed by stereoconservative hydroxyalkylation and condensation with chiral hydroxyamines or diamines. The ligands feature tunable steric protection of the alkoxide donor site and form a 7-membered chelate ring in the metal catalysts derived from these ligands. A total of 18 different ligands with varying electronic and steric properties were prepared and fully characterized by NMR, IR, mass spectroscopy, and single crystal structure analysis. Ferrocenealdehyde plays a crucial role as a key starting material for the synthesis of the novel chiral ligands. Specifically, ferrocenealdehyde (1a) and its pentamethyl derivative (1b) are used to initiate the modular synthetic sequence that leads to the formation of the chiral tridentate [NO2]H2 and tetradentate [N2O2]H2 Schiff base ligands.