393851

Sigma-Aldrich

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

97%

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

Quality Level

assay

97%

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

Related Categories

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.

Packaging

1 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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...
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)
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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