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1,1'-Ferrocenediisocyanate

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1,1'-Ferrocenediisocyanate
Names
IUPAC name 1,1'-diisocyanatoferrocene
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
InChI
  • InChI=1S/2C6H4NO.Fe/c2*8-5-7-6-3-1-2-4-6;/h2*1-4H;/q2*-1;+2Key: ARBUNVSYNOZTEE-UHFFFAOYSA-N
SMILES
  • C1=C(C=C1)N=C=O.C1=C(C=C1)N=C=O.
Properties
Chemical formula C12H8FeN2O2
Molar mass 268.053 g·mol
Appearance Yellow-brown solid
Density 1.633 g/cm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,1'-Ferrocenediisocyanate (1,1'-diisocyanatoferrocene) is the organoiron compound with the formula Fe(C5H4NCO)2. It is the simplest diisocyanate derivative of ferrocene. It can be synthesized by the Curtius rearrangement of the diacyl azide, using several protocols starting from 1,1'-ferrocenedicarboxylic acid. The compound is useful as an intermediate in the synthesis of 1,1'-diaminoferrocene by hydrolysis of the isocyanates. Various poly(siloxane–urethane) crosslinked polymers can be formed by reaction with siloxane-diols. These compounds are of interest as electrochemically active polymers that might have good mechanical properties at low temperature.

References

  1. ^ 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.
  2. Dascalu, Mihaela; Musteata, Valentina E.; Vacareanu, Loredana; Racles, Carmen; Cazacu, Maria (2015). "Synthesis and characterization of metal-containing poly(siloxane-urethane) crosslinked structures derived from siloxane diols and ferrocene diisocyanate". RSC Advances. 5 (120): 99193–99200. Bibcode:2015RSCAd...599193D. doi:10.1039/C5RA15290A.
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