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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

Assay

97%

form

solid

mp

128-130 °C (lit.)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Binuclear metal complexes. 1. Dicopper (II) complexes with binucleating ligands derived from 2-hydroxy-5-methylisophthalaldehyde and 2-(2-aminoethyl) pyridine or histamine.
Grzybowski JJ, et al
Inorganic Chemistry, 17(11), 3078-3082 (1978)
Jian Gao et al.
Inorganic chemistry, 44(2), 232-241 (2005-01-18)
A family of novel chiral "calixsalen" Schiff base macrocycles R,R-H(3)L4, R,R-H(3)L5, containing three chiral diamino moieties were synthesized by an efficient self-assembly and characterized by (1)H and (13)C NMR, mass spectrometry, and X-ray diffraction. The systematic synthesis, structure, and coordination
Bimetallic copper (II) and zinc (II) complexes of acyclic Schiff base ligands derived from amino acids.
Arbaoui A, et al
Inorgorganica Chimica Acta, 365(1), 96-102 (2011)
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)

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