Diformylcresol

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
Names
IUPAC name
2-hydroxy-5-methylisophthalaldehyde
Other names
2,6-diformyl-4-methylphenol
2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.971
EC Number
  • 230-768-4
UNII
  • InChI=1S/C9H8O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-5,12H,1H3
    Key: ZBOUXALQDLLARY-UHFFFAOYSA-N
  • CC1=CC(=C(C(=C1)C=O)O)C=O
Properties
C9H8O3
Molar mass 164.160 g·mol−1
Appearance white solid
Density 1.433 g/cm3[1]
Melting point 113 °C (235 °F; 386 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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 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]

References
  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 CuICuII 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.
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