1291-47-0

Usage

Uses

Used in Fuel Industry:
1,1'-DIMETHYLFERROCENE is used as a combustion control additive for improving the efficiency and performance of fuels. Its presence in the fuel helps regulate the combustion process, leading to better energy output and reduced emissions.
Used in Automotive Industry:
As an antiknock agent in gasoline, 1,1'-DIMETHYLFERROCENE helps prevent engine knocking or pinging, which can cause damage to the engine components. By increasing the fuel's octane rating, it allows for a smoother and more efficient combustion process, ultimately enhancing the vehicle's performance.
Used in Lubricant Industry:
1,1'-DIMETHYLFERROCENE is used for heat stabilization in greases, ensuring that the lubricants maintain their viscosity and performance even under high-temperature conditions. This property is crucial for industrial applications where machinery operates at elevated temperatures, requiring reliable and long-lasting lubrication.
Used in Plastics Industry:
In the plastics industry, 1,1'-DIMETHYLFERROCENE serves as a heat stabilizer, preventing the degradation of plastic materials when exposed to high temperatures during processing or in their end-use applications. This helps maintain the structural integrity and durability of the plastic products.
Used in Chemical Synthesis:
1,1'-DIMETHYLFERROCENE is used as a catalyst in the synthesis of ammonia, an essential compound in the production of fertilizers, nitric acid, and various other chemicals. Its catalytic properties enable a more efficient and cost-effective production process.
Used in Polymerization Processes:
1,1'-DIMETHYLFERROCENE is also utilized as a catalyst in polymerization reactions, where it helps initiate and control the formation of polymer chains. Its use in this application contributes to the development of new materials with specific properties and applications in various industries, such as automotive, electronics, and packaging.

Upstream product

• 1271-48-3 1,1'-ferrocenyldicarboxaldehyde 
• 7681-82-5 sodium iodide 
• 14362-44-8 iodide 
• 109-97-7 pyrrole 
• 7439-89-6 iron 
• 13292-87-0 dimethylsulfide borane complex 
• 7697-45-2 sodium pyrrolide 
• 25895-60-7 sodium cyanoborohydride 
• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 
• 12156-05-7 1,2-diferrocenylethane 

Downstream Products

• 45847-02-7 cumyl hydroperoxide anion 
• 7722-84-1 dihydrogen peroxide 
• 105694-20-0 hydroxo(5,10,15,20-tetramesitylporphyrinato)manganese(III) 
• 262280-87-5 5,10,15-tris(pentafluorophenyl)corrolato-manganese(III) 
• 1173294-15-9 5,10,15-tris(4-nitrophenyl)corrolatomanganese(III) 
• 1251825-86-1 (5,10,15-tris(3,5-bis(trifluoromethyl)phenyl)corrolato)manganese(III) 
• 123264-20-0 [(η(5)-C5H4Me)2Fe][B(C6H5)4] 
• 17632-84-7 Cr(II)(2,2'-bipyridine)3 
• 14900-04-0 triiodide^(1-) 

Relevant academic research and scientific papers

Studies on polyhalides. 31 on 1,1′-dimethylferriciniumpolyiodides [(MeH4C5)2Fe]Ix with x = 3, 5: Preparation and crystal structures of a triiodide (diMeFc)I3 and a pentaiodide (diMeFc)I5

Dimethylferrocene (diMeFc) may be oxidized by iodine analogous to ferrocene (Fc) and decamethylferrocene (DMFc) to the dimethylferrocenium ion (diMeFc)+ and precipitated as crystalline solids dimethylferrocenium triiodide (diMeFc)I3, dimethylferrocenium pentaiodide (diMeFc)I5 and dimethylferrocenium heptaiodide (diMeFc)I7. The two compounds with higher iodine content are new. The first two compounds are characterized by X-ray diffraction methods on single crystals. The structures are built up from complex cations with ecliptic conformation and isolated triiodide ions or remarkably concatenated pentaiodide ions. Dimethylferrocenium triiodide C12H14FeI3 crystallizes triclinically in P1? with a = 743.3(2) pm, b = 796.8(2) pm, c = 1471.7(4) pm, α = 98.53(2)°, β = 97.30(2)°, γ = 109.50° and Z = 2. The already known simple crystal structure may now be described without disordered anions. Dimethylferrocenium pentaiodide C12H14FeI5 crystallizes orthorhombically in Pnna with a = 1807.7(6) pm, b = 1543.4(10) pm, c = 1413.0(11) pm and Z = 8. The crystal structure contains pentaiodide chains 1∞[I3- · ? I2] with alternating planar and helical regions.

Oxidation of iodide by a series of Fe(III) complexes in acetonitrile

The oxidations of iodide by [FeIII(bpy)2(CN) 2]NO3, [FeIII(dmbpy)2(CN) 2]NO3, [FeIII(CH3Cp) 2]PF6, and [FeIII(5-Cl-phen) 2-(CN)2]NO3 at 25°C, ionic strength of 0.10 M in acetonitrile, are catalyzed by trace levels of copper ions. This copper catalysis can be effectively masked with the addition of 5.0 mM 2,2′-bipyridine (bpy), which permits the rate law of the direct reactions to be determined: -d[Fe(III)]/dt = 2(k1[1-] + k 2[l-]2)[Fe(III)]. According to 1H NMR and UV-vis spectra, the products of the reaction are I3 - and the corresponding Fe(II) complexes, with the stoichiometric ratio (Δ[I3-] /Δ[Fe(II)]) of 1:2. Linear free-energy relationships (LFERs) are obtained for both log k1 and log k2 vs E1/2 with slopes of 16.1 and 13.3 V -1, respectively. A mechanism is inferred in which k1 corresponds to simple electron transfer to form I. plus Fe(II), while k2 leads directly to I2-.. From the mild kinetic inhibition of the k1 path by [FeII(bpy) 2(CN)2] the standard potential (E°) of l ./l- is derived: E° = 0.60 ± 0.01 V (vs [Fe(Cp)2]+/0).

Spin-Doctoring Cobalt Redox Shuttles for Dye-Sensitized Solar Cells

A new low-spin (LS) cobalt(II) outer-sphere redox shuttle (OSRS) [Co(PY5Me2)(CN)]+, where PY5Me2 represents the pentadentate ligand 2,6-bis(1,1-bis(2-pyridyl)ethyl)pyridine, has been synthesized and characterized for its potential application in dye-sensitized solar cells (DSSCs). Introduction of the strong field CN- ligand into the open axial coordination site forced the cobalt(II) complex, [Co(PY5Me2)(CN)]+, to become LS based upon the complex's magnetic susceptibility (1.91 ± 0.02 μB), determined by the Evans method. Interestingly, dimerization and subsequent cobalt hexacyanide cluster formation of the [Co(PY5Me2)(CN)]+ monomer was observed upon long-term solvent exposure or addition of a supporting electrolyte for electrochemical characterization. Although long-term stability of the [Co(PY5Me2)(CN)]+ complex made it difficult to fabricate liquid electrolytes for DSSC applications, short-term stability in neat solvent afforded the opportunity to isolate the self-exchange kinetics of [Co(PY5Me2)(CN)]2+/+ via stopped-flow spectroscopy. Use of Marcus theory provided a smaller than expected self-exchange rate constant of 20 ± 5.5 M-1 s-1 for [Co(PY5Me2)(CN)]2+/+, which we attribute to a Jahn-Teller effect observed from the collected monomer crystallographic data. When compared side-by-side to cobalt tris(2,2′-bipyridine), [Co(bpy)3]3+, DSSCs employing [Co(PY5Me2)(CN)]2+ are expected to achieve superior charge collection, which result from a smaller rate constant, ket, for recombination based upon simple dark J-E measurements of the two redox shuttles. Given the negative redox potential (0.254 V vs NHE) of [Co(PY5Me2)(CN)]2+/+ and the slow recombination kinetics, [Co(PY5Me2)(CN)]2+/+ becomes an attractive OSRS to regenerate near IR absorbing sensitizers in solid-state DSSC devices.

Highly efficient reduction of ferrocenyl derivatives by borane

Borane, as a DMS or a THF complex, can efficiently reduce a large range of ferrocenyl derivatives (aldehydes, ketones, ethers, acetals, carboxylic acids, esters,...) if they bear at least one oxygen at a carbon at the α position. On the contrary, similar molecules, which contain nitrogen instead of oxygen, do not react with borane.

Reductive deoxygenation of α-ferrocenyl carbonyls and alcohols to alkylferrocenes by borane-dimethyl sulfide

The reductive deoxygenation of α-ferrocenyl aldehydes, ketones, alcohols, and carboxylic acid into the corresponding alkylferrocenes is accomplished solely by borane-dimethyl sulfide (BMS) in the absence of any Lewis acid catalyst. This is the first example of such reactivity of BMS. The present method allows the synthesis of alkylferrocenes including those bearing terminally functionalized pendant chains.

Solid-state mechanochemical synthesis of ferrocene

Solid-state mechanochemical reactions of iron(II) chloride with cyclopentadienides of alkaline metals or thallium, which lead to the formation of ferrocene, were studied. The dependence of the yield of the product on the parameters of mechanical loading f

Improvements in the preparation of cyclopentadienyl thallium and methylcyclopentadienylthallium and in their use in organometallic chemistry

Improved preparation methods of cyclopentadienylthallium and methylcyclopentadienylthallium, giving quantitative yields and incorporating ultrasound techniques, are described. Their use as starting materials for a wide range of organometallic syntheses is discussed and demonstrated.

An expedient, mild, reductive method for the preparation of alkylferrocenes

Reductive deoxygenation of acylferrocenes to the corresponding alkylferrocenes proceeded in excellent yields on utilizing a combination of sodium cyanotrihydroborate and boron trifluoride-diethyl ether.This method allows the synthesis of alkylferrocenes with functionalized tethers and is adaptable to large-scale preparations.

Simple reduction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoroacetic acid: New, efficient, general preparation of alkylferrocenes

Alkylferrocenes are obtained in excellent yields by ionic hydrogenation of ferrocenyl aldehydes and ketones using sodium boranuide and trifluoroacetic acid.

Ionic hydrogenation of acylferrocenes using zinc borohydride: An efficient, mild method for the preparation of alkylferrocenes

An effective mild procedure for the reductive deoxygenation of α-ferrocenyl aldehydes, ketones, and alcohols into the corresponding alkylferrocenes is described using a combination of zinc borohydride and zinc chloride. This is the first example of such reactivity of zinc borohydride. The present method allows the synthesis of alkylferrocenes bearing terminally functionalized pendant chains.