128925-12-2

Basic information

• Product Name: 1-formyl-2,2′,3,3′,4,4′5,5′-octamethylferrocene
• Synonyms: 1-formyl-2,2′,3,3′,4,4′5,5′-octamethylferrocene
• CAS NO: 128925-12-2
• Molecular Weight: 326.262
• Mol File: 128925-12-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-formyl-2,2′,3,3′,4,4′5,5′-octamethylferrocene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-formyl-2,2′,3,3′,4,4′5,5′-octamethylferrocene(128925-12-2)
• EPA Substance Registry System: 1-formyl-2,2′,3,3′,4,4′5,5′-octamethylferrocene(128925-12-2)

Safety Data

• Hazardous Substances Data: 128925-12-2(Hazardous Substances Data)

Upstream product

• 59568-28-4 1,1',2,2',3,3',4,4'-octamethylferrocene 
• 68-12-2 N,N-dimethyl-formamide 
• 127-09-3 sodium acetate 

Downstream Products

• 1425938-44-8 C₃₉H₂₈Cl₁₄Fe 

Relevant articles and documents

Synthesis, characterization and electrochemical behaviour of dimethyleneamine-bridged methylated and non-methylated biferrocenyl derivatives

Two dimethyleneamine-bridged octamethylated and non-methylated biferrocenyl complexes, compounds 1 and 2, have been synthesized and characterized by 1H, 29Si{1H} and 13C{1H} NMR spectroscopy, and mass spectrometry. The redox activity of the ferrocenyl centers in 1 and 2 has been characterized by cyclic voltammetry in dichloromethane containing [n-Bu4N][PF6], [n-Bu4N][B(C6F5)4] or [n-Bu4N]Cl as electrolyte support. Their electrochemistry is not only strongly dependent on the solvent/electrolyte medium but also on the substituents of the ferrocenyl moieties. Studies of the electrochemical oxidation of 1 provide evidence of the grafting of a ferrocene species onto platinum electrode surfaces.

Stepwise synthesis of octamethylferrocene-1,1′-dicarbaldehyde. Preparation of new electron donors for charge-transfer complexes

A stepwise synthesis of octamethylferrocene-1,1′-dicarbaldehyde (3), starting from 1,2,3,4-tetramethyl-5-(methoxycarbonyl)cyclopentadiene (7) is described, involving ferrocene formation, ester reduction to the corresponding bis(hydroxymethyl) derivative 9, and MnO2 oxidation. The aldehyde 3 readily reacts with different phosphonates derived from sulfurcontaining heterocycles in a Wittig-Horner reaction to form new electron donors that may be used in the preparation of various charge transfer complexes. The X-ray crystal structures of 1-[(1,3-benzodithiol-2-ylidene)methyl]-2,2′,3,3′,4,4′,5, 5′-octamethylferrocene (11a), 1-[(1,3-dithiolo[4,5-b][1,3]dithiol-2-ylidene)methyl]-2,2′,3,3′,4, 4′,5,5′-octamethylferrocene (11b), 1,1′-bis[(1,3-benzodithiol-2-ylidene)methyl]-2,2′,3,3′,4, 4′,5,5′-octamethylferrocene (12a), and 1,1′-bis[(5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiol-2-ylidene)methyl]-2, 2′,3,3′,4,4′,5,5′-octamethylferrocene (12c) have been determined. In these compounds the planes of the sulfur heterocycles are oriented at angles of 60-75°, with respect to the plane of the respective Cp ring.

Synthesis of octamethylferrocene derivatives via reaction of (octamethylferrocenyl)methyl carbocation with nucleophiles and application to functionalization of surfaces

Formylation of octamethylferrocene, Fe(C5Me4H)2, using N,N'-dimethylformamide/OPCI3 in CHCI3 solvent at 60-70 °C gives octamethylformylferrocene in high yield (～95%). The aldehyde can be converted to a CN group to give octamethylcyanoferrocene or can be used to prepare ethyl 0-(octamethylferrocenyl)acrylate. Most important, reductionn of octamethylformylferrocene using LiAIH4 in Et2O yields the alcohol in ～95% yield. Acid-catalyzed (HBF4) dehydration of the alcohol. III, leads to formation of (octamethylferrocenyl)methyl carbocation in almost quantitative yield. The carbocation I can be isolated as an orange-red BF4- salt in ～ 90% yield from octamethylferrocene. I shows sharp 13C and 1H NMR spectral features consistent with formulation as a diamagnetic Fe(II) species with the positive charge localized on the C having two H's. I slowly dimerizes, even in the solid state, to a C-C coupled product with two Fe(III) centers. The paramagnetic, blue-green dimer can be reduced with cobaltocene or aqueous Na2S2O4 to l,2-bis(octamethylferrocenyl)ethane. Reaction of (octamethylferrocenyl)methyl carbocation with nucleophiles is a convenient synthetic route to octamethylferrocene derivatives, which have proved difficult to obtain by electrophilic substitution of octamethylferrocene. Reaction of the new carbocation I has been used to synthesize octamethylferrocenyl derivatives in good to excellent yields (～60-95%) via reaction with amines, thiols, or CN- Reaction of (octamethylferrocenyl)methyl carbocation with surface-confined nucleophiles such as NH2 or SH [surfaces derivatized with (MeO)3Si(CH2)3NH2 or (MeO)3Si(CH2)3SH] is a convenient way to attach octamethylferrocene derivatives to surfaces including SiO2, Pt, and indium tin oxide (ITO).