1,1'-Dimethylferrocen

Base Information

• Chemical Name: 1,1'-Dimethylferrocen
• CAS No.: 1291-47-0
• Molecular Formula: C12H14Fe
• Molecular Weight: 214.09
• Hs Code.: 29319090
• Mol file: 1291-47-0.mol

Synonyms:1,1'-Dimethylferrocen;D1273

Chemical Property of 1,1'-Dimethylferrocen

Chemical Property:

• Appearance/Colour: dark orange crystals
• Melting Point: 37-40 °C(lit.)
• Boiling Point: 70-80 °C(Press: 2 Torr)
• Flash Point: 226 °F
• PSA: 0.00000
• Density: 1.2349 g/cm3(Temp: 35 °C)
• LogP: 2.82070
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: air sensitive
• Water Solubility.: Slightly soluble in methanol. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 214.044486
• Heavy Atom Count: 13
• Complexity: 97.7

Purity/Quality:

98% ^*data from raw suppliers

1,1''-Dimethylferrocene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C[CH-]1.CC1=CC=C[CH-]1.[Fe+2]
• Uses: It is used as a combustion control additive in fuels, antiknock agent in gasoline, and for heat stabilization in greases and plastics. It is used as a catalyst for synthesis of ammonia, polymerization.

Technology Process of 1,1'-Dimethylferrocen

There total 23 articles about 1,1'-Dimethylferrocen 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: 96.0%

1,1'-ferrocenyldicarboxaldehyde (1271-48-3) + borane tetrahydrofuran → 1,1'-dimethylferrocene (1291-47-0)

Guidance literature:

In tetrahydrofuran; 6 equiv of borane, THF, reflux, 15 min;

DOI:10.1016/S0022-328X(01)00936-6

Reference yield: 95.0%

1,1'-ferrocenyldicarboxaldehyde (1271-48-3) + dimethylsulfide borane complex (13292-87-0) → 1,1'-dimethylferrocene (1291-47-0)

Guidance literature:

In dichloromethane; all manipulations under Ar atm.; to soln. of ferrocenyl compd. added equiv. amt. of soln. of B compd. in CH2Cl2, stirred at room temp. for 3 h; quenched with aq. NH4Cl, org. layer sepd., aq. layer extd. with CH2Cl2,combined org. extracts dried over anhyd. MgSO4, solvent removed in vac., chromy., elem. anal.;

Reference yield: 95.0%

1,1'-dihydroxymethylferrocene + dimethylsulfide borane complex (13292-87-0) → 1,1'-dimethylferrocene (1291-47-0)

Guidance literature:

In dichloromethane; all manipulations under Ar atm.; to soln. of ferrocenyl compd. added equiv. amt. of soln. of B compd. in CH2Cl2, stirred at room temp. for 3 h; quenched with aq. NH4Cl, org. layer sepd., aq. layer extd. with CH2Cl2,combined org. extracts dried over anhyd. MgSO4, solvent removed in vac., chromy., elem. anal.;

upstream raw materials:

1,1'-ferrocenyldicarboxaldehyde

sodium iodide

iodide

pyrrole

Downstream raw materials:

cumyl hydroperoxide anion

triiodide^(1-)

Cr(II)(2,2'-bipyridine)3

(5,10,15-tris(3,5-bis(trifluoromethyl)phenyl)corrolato)manganese(III)

Refernces

• 1、 Wang, Xiaoguang,Stanbury, David M.. "Oxidation of iodide by a series of Fe(III) complexes in acetonitrile". . p. 3415 - 3423. Retrieved 2006.
• 2、 Baillargeon, Josh,Xie, Yuling,Raithel, Austin L.,Ghaffari, Behnaz,Staples, Richard J.,Hamann, Thomas W.. "Spin-Doctoring Cobalt Redox Shuttles for Dye-Sensitized Solar Cells". supporting information. p. 11633 - 11645. Retrieved 2018/09/12.
• 3、 Kim, Dong-Hoo,Ryu, Eun-Sook,Cho, Chan Sik,Shim, Sang Chul,Kim, Hong-Seok,Kim, Tae-Jeong. "Reductive deoxygenation of α-ferrocenyl carbonyls and alcohols to alkylferrocenes by borane-dimethyl sulfide". . p. 5784 - 5786. Retrieved 2008/10/08.