1,1'-Diaminoferrocene

1,1'-Diaminoferrocene
Names
	IUPAC name 1,1'-Diaminoferrocene
	Systematic IUPAC name Ferrocene-1,1'-diamine
Identifiers
CAS Number	41636-79-7;
3D model (JSmol)	Interactive image;
PubChem CID	15912376;
	InChI InChI=1S/2C5H6N.Fe/c26-5-3-1-2-4-5;/h21-4H,6H2;/q2*-1;+2 Key: VEDYBWCXQCEXEB-UHFFFAOYSA-N;
	SMILES C1=C[C-](C=C1)N.C1=C[C-](C=C1)N.[Fe+2];
Properties
Chemical formula	C10H12FeN2
Molar mass	216.065 g·mol−1
Appearance	yellow solid
Density	1.644 g/cm3
Melting point	183–186 °C (361–367 °F; 456–459 K)
Boiling point	decomposition
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,1'-Diaminoferrocene is the organoiron compound with the formula Fe(C₅H₄NH₂)₂. It is the simplest diamine derivative of ferrocene. It is a yellow, air-sensitive solid that is soluble in aqueous acid. The 1,1' part of its name refers to the location of the amine groups on separate rings. Compared to the parent ferrocene, the diamine is about 600 mV more reducing.^[1]

It can be prepared from the diisocyanate Fe(C₅H₄NCO)₂, which in turn is derived from 1,1'-ferrocenedicarboxylic acid.^[2] 1,1'-Diaminoferrocene was originally prepared by hydrogenation of 1,1'-diazidoferrocene ( Fe(C₅H₄N₃)₂).^[1]

1,1'-Diaminoferrocene has been incorporated into various diamide and diimine ligands, which form catalysts that exhibit redox switching.^[3]

References

^ ^a ^b ^c Shafir, Alexandr; Power, Maurice P.; Whitener, Glenn D.; Arnold, John (2000). "Synthesis, Structure, and Properties of 1,1'-Diamino- and 1,1'-Diazidoferrocene". Organometallics. 19 (19): 3978–3982. doi:10.1021/om0004085.
^ Petrov, Alex R.; Jess, Kristof; Freytag, Matthias; Jones, Peter G.; Tamm, Matthias (2013). "Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted Ferrocene Derivatives". Organometallics. 32 (20): 5946–5954. doi:10.1021/om4004972.
^ Wang, Xinke; Thevenon, Arnaud; Brosmer, Jonathan L.; Yu, Insun; Khan, Saeed I.; Mehrkhodavandi, Parisa; Diaconescu, Paula L. (2014). "Redox Control of Group 4 Metal Ring-Opening Polymerization Activity toward l-Lactide and ε-Caprolactone". Journal of the American Chemical Society. 136 (32): 11264–11267. doi:10.1021/ja505883u. PMID 25062499. S2CID 22098566.

[JA-1] Shafir, Alexandr; Power, Maurice P.; Whitener, Glenn D.; Arnold, John (2000). "Synthesis, Structure, and Properties of 1,1'-Diamino- and 1,1'-Diazidoferrocene". Organometallics. 19 (19): 3978–3982. doi:10.1021/om0004085.

[2] Petrov, Alex R.; Jess, Kristof; Freytag, Matthias; Jones, Peter G.; Tamm, Matthias (2013). "Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted Ferrocene Derivatives". Organometallics. 32 (20): 5946–5954. doi:10.1021/om4004972.

[3] Wang, Xinke; Thevenon, Arnaud; Brosmer, Jonathan L.; Yu, Insun; Khan, Saeed I.; Mehrkhodavandi, Parisa; Diaconescu, Paula L. (2014). "Redox Control of Group 4 Metal Ring-Opening Polymerization Activity toward l-Lactide and ε-Caprolactone". Journal of the American Chemical Society. 136 (32): 11264–11267. doi:10.1021/ja505883u. PMID 25062499. S2CID 22098566.

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