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N,N-Dimethylaminomethylferrocene

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N,N-Dimethylaminomethylferrocene
Names
IUPAC name N,N-Dimethylaminomethylferrocene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 215-044-8
PubChem CID
InChI
  • InChI=1S/C8H12N.C5H5.Fe/c1-9(2)7-8-5-3-4-6-8;1-2-4-5-3-1;/h3-6H,7H2,1-2H3;1-5H;/q2*-1;+2Key: ISDNRMKSXGICTM-UHFFFAOYSA-N
SMILES
  • CN(C)Cc1ccc1.1cccc1.
Properties
Chemical formula C13H17FeN
Molar mass 243.131 g·mol
Appearance orange oil
Melting point 5–8 °C (41–46 °F; 278–281 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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:

(C5H5)2Fe + CH2O + HN(CH3)2 → (C5H5)Fe(C5H4CH2N(CH3)2 + H2O

It is a precursor to prototypes of ferrocene-containing redox sensors and diverse ligands.

The amine can be quaternized, which provides access to many derivatives.

References

  1. Lednicer, Daniel; Hauser, Charles R. (1960). "N,N-Dimethylaminomethylferrocene Methiodide". Organic Syntheses. 40: 31. doi:10.15227/orgsyn.040.0031.
  2. 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. (1984). "Ferrocene-mediated enzyme electrode for amperometric determination of glucose". Analytical Chemistry. 56 (4): 667–671. doi:10.1021/ac00268a018. PMID 6721151.
  3. Gao, De-Wei; Shi, Yan-Chao; Gu, Qing; Zhao, Zheng-Le; You, Shu-Li (2013). "Enantioselective Synthesis of Planar Chiral Ferrocenes via Palladium-Catalyzed Direct Coupling with Arylboronic Acids". Journal of the American Chemical Society. 135 (1): 86–89. doi:10.1021/ja311082u. PMID 23253097.
  4. Lednicer, Daniel; Mashburn Jr., T. Arthur; Hauser, Charles R. (1960). "Hydroxymethylferrocene". Organic Syntheses. 40: 52. doi:10.15227/orgsyn.040.0052.
  5. Lednicer, Daniel; Hauser, Charles R. (1960). "Ferrocenylacetonitrile". Organic Syntheses. 40: 45. doi:10.15227/orgsyn.040.0045.
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