N,N-Dimethylaminomethylferrocene

N,N-Dimethylaminomethylferrocene
Names
	IUPAC name N,N-Dimethylaminomethylferrocene
Identifiers
CAS Number	1271-86-9;
3D model (JSmol)	Interactive image;
ChemSpider	92220;
EC Number	215-044-8;
PubChem CID	102082;
	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;+2 Key: ISDNRMKSXGICTM-UHFFFAOYSA-N;
	SMILES CN(C)Cc1[cH-]ccc1.[cH-]1cccc1.[Fe+2];
Properties
Chemical formula	C13H17FeN
Molar mass	243.131 g·mol−1
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 [77 °F], 100 kPa). Infobox references

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 + H₂O

It is a precursor to prototypes of ferrocene-containing redox sensors^[2] and diverse ligands.^[3]

The amine can be quaternized,^[1] which provides access to many derivatives.^[4]^[5]

References

^ ^a ^b Lednicer, Daniel; Hauser, Charles R. (1960). "N,N-Dimethylaminomethylferrocene Methiodide". Organic Syntheses. 40: 31. doi:10.15227/orgsyn.040.0031.
^ 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.
^ 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.
^ Lednicer, Daniel; Hauser, Charles R. (1960). "Ferrocenylacetonitrile". Organic Syntheses. 40: 45. doi:10.15227/orgsyn.040.0045.
^ Lednicer, Daniel; Mashburn Jr., T. Arthur; Hauser, Charles R. (1960). "Hydroxymethylferrocene". Organic Syntheses. 40: 52. doi:10.15227/orgsyn.040.0052.

[OrgSynth-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; Hauser, Charles R. (1960). "Ferrocenylacetonitrile". Organic Syntheses. 40: 45. doi:10.15227/orgsyn.040.0045.

[5] Lednicer, Daniel; Mashburn Jr., T. Arthur; Hauser, Charles R. (1960). "Hydroxymethylferrocene". Organic Syntheses. 40: 52. doi:10.15227/orgsyn.040.0052.

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