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393851

Sigma-Aldrich

2-Hydroxy-5-methyl-1,3-benzenedicarboxaldehyde

97%

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About This Item

Linear Formula:
HOC6H2(CH3)(CHO)2
CAS Number:
Molecular Weight:
164.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

128-130 °C (lit.)

functional group

aldehyde

SMILES string

Cc1cc(C=O)c(O)c(C=O)c1

InChI

1S/C9H8O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-5,12H,1H3

InChI key

ZBOUXALQDLLARY-UHFFFAOYSA-N

General description

2-Hydroxy-5-methyl-1,3-benzenedicarboxaldehyde (2-hydroxy-5-methylisophthalaldehyde) is a dialdehyde derivative. It has been synthesized by heating p-cresol with hexamethylenetetramine. The structure has been confirmed by 1H and 13C NMR. It is an important raw material for the synthesis of various binucleating schiff base ligand.

Application

2-Hydroxy-5-methyl-1,3-benzenedicarboxaldehyde (2-hydroxy-5-methylisophthalaldehyde) is suitable reagent used in the synthesis of 2-(2′-vinyloxyethoxy)-5-methylisophthaldehyde and chiral calixsalen macrocycles.
2-Hydroxy-5-methyl-1,3-benzenedicarboxaldehyde may be used in the synthesis of the following:
  • 3-[(2,4-Dichlorophenyl)iminomethyl]-2-hydroxy-5-methylbenzaldehyde, a Schiff base.
  • 2-Hydroxy-3-methoxymethyl-5-methylbenzaldehyde.
  • Acyclic Schiff-base ligands.
  • Macrobicyclic ligands (MSB).
  • 4-Methyl-2,6-divinylphenol.
  • 2-Hydroxy-3-dimethoxymethyl-5-methylbenzaldehyde.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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3-[(2, 4-Dichlorophenyl) iminomethyl]-2-hydroxy-5-methylbenzaldehyde.
Kilic I, et al
Acta Crystallographica Section E, Structure Reports Online, 65(6), 1347-1347 (2009)
2-Hydroxy-3-methoxymethyl-5-methylbenzaldehyde.
Gunasekaran B, et al
Acta Crystallographica Section E, Structure Reports Online, 69(2), 317-317 (2013)
ESI MS, spectroscopic and semiempirical characterization of a macrobicyclic complex with Er (III) cation.
Przybylski P, et al.
Journal of Molecular Structure, 878(1), 95-103 (2008)
Steric effect in the free radical polymerization of vinyl ethers containing electron-deficient olefin groups.
Lee JY and Jin MK
Polymer Bull., 44(3), 2777-2284 (2000)
New efficient ruthenium metathesis catalyst containing chromenyl ligand.
Hryniewicka A, et al
Journal of Organometallic Chemistry, 695(9), 1265-1270 (2010)

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