Diformylcresol

Diformylcresol
Names
	IUPAC name 2-hydroxy-5-methylisophthalaldehyde
	Other names 2,6-diformyl-4-methylphenol; 2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde
Identifiers
CAS Number	7310-95-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3904097;
ChemSpider	73760;
ECHA InfoCard	100.027.971
EC Number	230-768-4;
PubChem CID	81744;
UNII	V6R37R6AU3 ;
CompTox Dashboard (EPA)	DTXSID60223374 ;
	InChI InChI=1S/C9H8O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-5,12H,1H3 Key: ZBOUXALQDLLARY-UHFFFAOYSA-N;
	SMILES CC1=CC(=C(C(=C1)C=O)O)C=O;
Properties
Chemical formula	C9H8O3
Molar mass	164.160 g·mol−1
Appearance	white solid
Density	1.433 g/cm3
Melting point	113 °C (235 °F; 386 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diformylcresol is an organic compound with the formula CH₃C₆H₂(CHO)₂OH. The 2,6-diformyl derivative of p-cresol is the most common isomer and is a white solid at room temperature.

Diformylcresol condenses with amines to give diimines that are widely studied as binucleating ligands.^[2]^[3]

Synthesis

Formyl groups (aldehydes) are fairly strong deactivating groups for electrophilic aromatic substitution reactions, hence double-addition to a phenol requires forcing conditions. Diformylcresol may be prepared from p-cresol by the Reimer-Tiemann reaction or the Duff reaction.^[4]

The corresponding reaction of phenol would be expected to lead to formylation of the 4-position vs 2,6-selectivity.^[5]

Related compounds

salicylaldehyde, a phenol with only one flanking formyl group

References

^ Habarurema, Gratien; Gerber, Thomas I. A.; Hosten, Eric; Betz, Richard (2014). "Redetermination of the crystal structure of 2,6-diformyl-4-methylphenol, at 200 K, C9H8O3". Zeitschrift für Kristallographie - New Crystal Structures. 229 (4): 331–332. doi:10.1515/ncrs-2014-0171. S2CID 93304005.
^ Thompson, Laurence K.; Mandal, Sanat K.; Tandon, Santokh S.; Bridson, John N.; Park, Murray K. (1996). "Magnetostructural Correlations in Bis(μ₂-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling". Inorganic Chemistry. 35 (11): 3117–3125. doi:10.1021/IC9514197. PMID 11666507.
^ Gagne, R. R.; Spiro, C. L.; Smith, T. J.; Hamann, C. A.; Thies, W. R.; Shiemke, A. D. (1981). "The Synthesis, Redox Properties, and Ligand Binding of Heterobinuclear Transition-Metal Macrocyclic Ligand Complexes. Measurement of an Apparent Delocalization Energy in a Mixed-Valent Cu^ICu^II Complex". Journal of the American Chemical Society. 103 (14): 4073–4081. doi:10.1021/ja00404a017.
^ Lindoy, Leonard F. (July 1998). "Mono- and Diformylation of 4-Substituted Phenols: A New Application of the Duff Reaction". Synthesis. 1998 (7): 1029–1032. doi:10.1055/s-1998-2110.
^ Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3527306732.

[1] Habarurema, Gratien; Gerber, Thomas I. A.; Hosten, Eric; Betz, Richard (2014). "Redetermination of the crystal structure of 2,6-diformyl-4-methylphenol, at 200 K, C9H8O3". Zeitschrift für Kristallographie - New Crystal Structures. 229 (4): 331–332. doi:10.1515/ncrs-2014-0171. S2CID 93304005.

[2] Thompson, Laurence K.; Mandal, Sanat K.; Tandon, Santokh S.; Bridson, John N.; Park, Murray K. (1996). "Magnetostructural Correlations in Bis(μ₂-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling". Inorganic Chemistry. 35 (11): 3117–3125. doi:10.1021/IC9514197. PMID 11666507.

[3] Gagne, R. R.; Spiro, C. L.; Smith, T. J.; Hamann, C. A.; Thies, W. R.; Shiemke, A. D. (1981). "The Synthesis, Redox Properties, and Ligand Binding of Heterobinuclear Transition-Metal Macrocyclic Ligand Complexes. Measurement of an Apparent Delocalization Energy in a Mixed-Valent Cu^ICu^II Complex". Journal of the American Chemical Society. 103 (14): 4073–4081. doi:10.1021/ja00404a017.

[4] Lindoy, Leonard F. (July 1998). "Mono- and Diformylation of 4-Substituted Phenols: A New Application of the Duff Reaction". Synthesis. 1998 (7): 1029–1032. doi:10.1055/s-1998-2110.

[5] Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3527306732.

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