diformylcresol
{{Chembox
| ImageFile = Diformylcresol.svg
| ImageSize = 190
| ImageAlt =
| IUPACName = 2-hydroxy-5-methylisophthalaldehyde
| OtherNames = 2,6-diformyl-4-methylphenol
2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde
|Section1={{Chembox Identifiers
| CASNo = 7310-95-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V6R37R6AU3
| ChEMBL = 3904097
| ChemSpiderID = 73760
| EINECS = 230-768-4
| PubChem = 81744
| StdInChI=1S/C9H8O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-5,12H,1H3
| StdInChIKey = ZBOUXALQDLLARY-UHFFFAOYSA-N
| SMILES = CC1=CC(=C(C(=C1)C=O)O)C=O
}}
|Section2={{Chembox Properties
| C = 9 | H = 8 | O = 3
| MolarMass =
| Appearance = white solid
| MeltingPtC = 113
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite journal |doi=10.1021/IC9514197|title=Magnetostructural Correlations in Bis(μ2-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling|year=1996|last1=Thompson|first1=Laurence K.|last2=Mandal|first2=Sanat K.|last3=Tandon|first3=Santokh S.|last4=Bridson|first4=John N.|last5=Park|first5=Murray K.|journal=Inorganic Chemistry|volume=35|issue=11|pages=3117–3125|pmid=11666507}}{{cite journal |doi=10.1021/ja00404a017|title=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|year=1981|last1=Gagne|first1=R. R.|last2=Spiro|first2=C. L.|last3=Smith|first3=T. J.|last4=Hamann|first4=C. A.|last5=Thies|first5=W. R.|last6=Shiemke|first6=A. D.|journal=Journal of the American Chemical Society|volume=103|issue=14|pages=4073–4081}}
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.{{cite journal |last=Lindoy |first=Leonard F. |authorlink=Leonard Francis Lindoy |title=Mono- and Diformylation of 4-Substituted Phenols: A New Application of the Duff Reaction |journal=Synthesis |date=July 1998 |volume=1998 |issue=7 |pages=1029–1032 |doi=10.1055/s-1998-2110}}
The corresponding reaction of phenol would be expected to lead to formylation of the 4-position vs 2,6-selectivity.{{Ullmann | last1 = Brühne | first1 = Friedrich | last2 = Wright | first2 = Elaine | year = 2011 | title = Benzaldehyde | doi = 10.1002/14356007.a03_463.pub2}}
Related compounds
- salicylaldehyde, a phenol with only one flanking formyl group