Diformylcresol

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 Edit this at Wikidata
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
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).

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.

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.

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

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. ISBN 978-3-527-30673-2.