N,N-Dimethylaminomethylferrocene Explained

N,N-Dimethylaminomethylferrocene is the dimethylaminomethyl derivative of ferrocene, (C5H5)Fe(C5H4CH2N(CH3)2. It is an air-stable, dark-orange syrup that is soluble in common organic solvents. The compound is prepared by the reaction of ferrocene with formaldehyde and dimethylamine:[1]

(C5H5)2Fe + CH2O + HN(CH3)2 → (C5H5)Fe(C5H4CH2N(CH3)2 + H2OIt is a precursor to prototypes of ferrocene-containing redox sensors[2] and diverse ligands.[3]

The amine can be quaternized,[4] which provides access to many derivatives.[5]

References

  1. 10.15227/orgsyn.040.0031. N,N-Dimethylaminomethylferrocene Methiodide. Organic Syntheses. 1960. 40. 31. Daniel . Lednicer. Charles R.. Hauser.
  2. 10.1021/ac00268a018. Ferrocene-mediated enzyme electrode for amperometric determination of glucose. 1984. Cass. Anthony E. G.. Davis. Graham.. Francis. Graeme D.. Hill. H. Allen O.. Aston. William J.. Higgins. I. John.. Plotkin. Elliot V.. Scott. Lesley D. L.. Turner. Anthony P. F.. Analytical Chemistry. 56. 4. 667–671. 6721151.
  3. 10.1021/ja311082u. Enantioselective Synthesis of Planar Chiral Ferrocenes via Palladium-Catalyzed Direct Coupling with Arylboronic Acids. 2013. Gao. De-Wei. Shi. Yan-Chao. Gu. Qing. Zhao. Zheng-Le. You. Shu-Li. Journal of the American Chemical Society. 135. 1. 86–89. 23253097.
  4. 10.15227/orgsyn.040.0052. Hydroxymethylferrocene. Organic Syntheses. 1960. 40. 52. Daniel. Lednicer. T. Arthur . Mashburn Jr.. Charles R.. Hauser.
  5. 10.15227/orgsyn.040.0045. Ferrocenylacetonitrile. Organic Syntheses. 1960. 40. 45. Daniel . Lednicer. Charles R. . Hauser.

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