2,5-Furandicarboxaldehyde

2,5-Furandicarboxaldehyde
Names
	Other names Furan-2,5-dicarboxaldehyde, 2,5-Diformylfuran
Identifiers
CAS Number	823-82-5 ;
3D model (JSmol)	Interactive image;
Abbreviations	FDC
ChEBI	CHEBI:83385;
ChemSpider	63172;
ECHA InfoCard	100.011.382
EC Number	212-520-7;
KEGG	C20899;
PubChem CID	69980;
UNII	L4HT8N2Z72;
CompTox Dashboard (EPA)	DTXSID60231676 ;
	InChI InChI=1S/C6H4O3/c7-3-5-1-2-6(4-8)9-5/h1-4H Key: KUCOHFSKRZZVRO-UHFFFAOYSA-N;
	SMILES C1=C(OC(=C1)C=O)C=O;
Properties
Chemical formula	C6H4O3
Molar mass	124.095 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P305+P351+P338
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,5-Furandicarboxaldehyde (FDC) is an organic compound with the molecular formula C₄H₂O(CHO)₂. It consists of a furan ring with aldehyde groups on the 2 and 5 position. It is therefore classified as a dialdehyde.

Synthesis[edit]

2,5-Furandicarboxaldehyde is an oxidation product of 5-hydroxymethyl furfural (HMF), which in turn can be prepared from fructose. Alternatively, methods have been developed to convert fructose in one step to 2,5-furandicarboxaldehyde.^[1] The conversion from fructose to HMF and FDC can be performed relatively efficiently and following the principles of green chemistry. As such, these materials are often considered as "greener" bio-based alternatives.^{[citation needed]}

Applications[edit]

2,5-Furandicarboxaldehyde can be used in the preparation of polyimine vitrimers.^[2] It can also be applied as an alternative to glutaraldehyde as crosslinking agent for covalent enzyme immobilisation.^[3]

References[edit]

^ Zhou, C.; Zhao, J.; Sun, H.; Song, Y.; Wan, X.; Lin, H.; Yang, Y. (2019). "One-Step Approach to 2,5-Diformylfuran from Fructose over Molybdenum Oxides Supported on Carbon Spheres". ACS Sustainable Chem. Eng. 7 (1): 315–323. doi:10.1039/c6py01395c.
^ Dhers, S.; Vantomme, G.; Avérous, L. (2019). "A fully bio-based polyimine vitrimer derived from fructose" (PDF). Green Chemistry. 12 (7): 35676–35684. doi:10.1039/C9GC00540D. S2CID 104336119.
^ Danielli, C.; Van Langen, L.; Boes, D.; Asora, F.; Anselmi, S.; Provenza, F.; Renzi, M.; Gardossi, L. (2022). "2,5-Furandicarboxaldehyde as a bio-based crosslinking agent replacing glutaraldehyde for covalent enzyme immobilization". RSC Adv. 21 (7): 1596–1601. Bibcode:2022RSCAd..1235676D. doi:10.1039/D2RA07153C. PMC 9748790. PMID 36545099.

[1] Zhou, C.; Zhao, J.; Sun, H.; Song, Y.; Wan, X.; Lin, H.; Yang, Y. (2019). "One-Step Approach to 2,5-Diformylfuran from Fructose over Molybdenum Oxides Supported on Carbon Spheres". ACS Sustainable Chem. Eng. 7 (1): 315–323. doi:10.1039/c6py01395c.

[2] Dhers, S.; Vantomme, G.; Avérous, L. (2019). "A fully bio-based polyimine vitrimer derived from fructose" (PDF). Green Chemistry. 12 (7): 35676–35684. doi:10.1039/C9GC00540D. S2CID 104336119.

[3] Danielli, C.; Van Langen, L.; Boes, D.; Asora, F.; Anselmi, S.; Provenza, F.; Renzi, M.; Gardossi, L. (2022). "2,5-Furandicarboxaldehyde as a bio-based crosslinking agent replacing glutaraldehyde for covalent enzyme immobilization". RSC Adv. 21 (7): 1596–1601. Bibcode:2022RSCAd..1235676D. doi:10.1039/D2RA07153C. PMC 9748790. PMID 36545099.

[1]

[2]

[3]

Synthesis[edit]

Applications[edit]

See also[edit]

References[edit]