• 574-19-6 2'-Hydroxy-1'-acetonaphthone - AMI Scientific
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TCI

CAS 574-19-6

2'-Hydroxy-1'-acetonaphthone TCI H0936

2'-Hydroxy-1'-acetonaphthone TCI H0936
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Rp 2.333.100,00
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2'-Hydroxy-1'-acetonaphthone is a positional isomer of hydroxylated acetonaphthone, in which the acetyl group occupies position one and the hydroxyl group sits at position two of the naphthalene framework. This seemingly small difference in substitution pattern has a real effect on the steric environment surrounding the carbonyl group and on the direction in which cyclisation can proceed, so the compound complements its isomer as a building block option. In the laboratory it is used to construct fused oxygenated heterocyclic systems, chelating ligands, and molecules whose luminescent behaviour is influenced by internal hydrogen bonding.

The properties that make this material a preferred choice begin with the presence of adjacent hydroxyl and carbonyl groups, which form an intramolecular hydrogen bond and stabilise the molecular conformation. That stabilisation influences the acidity of the phenol, the chemical shifts observed in NMR spectra, and the absorption and emission behaviour of the compound. At the same time the acetyl group remains fully reactive towards cross aldol condensation, Claisen condensation, and the formation of carbonyl derivatives such as oximes or hydrazones. This combination of a conformationally locked scaffold and an available reactive handle gives synthetic chemists predictable control over subsequent transformations.

The material is supplied as a crystalline solid with good solubility in ethanol, methanol, acetone, chloroform, and dimethyl sulfoxide. In Indonesian laboratories this solubility profile suits the solvent systems ordinarily kept on hand in academic and industrial synthesis facilities, allowing the compound to be taken directly into solution for condensation work, ligand preparation, or spectroscopic study without specialised handling. Its role as a non-heterocyclic building block places it among the starting materials selected during route planning for oxygenated heterocycle targets.

  • Synthesis of fused oxygenated heterocycles: the ortho-positioned hydroxyl and acetyl pair provides both the nucleophilic oxygen and the electrophilic carbonyl needed for ring closure onto the naphthalene core.
  • Preparation of chelating ligands: the neighbouring hydroxyl and carbonyl functions present a natural donor arrangement for coordination chemistry, making the compound a direct entry point to bidentate ligand frameworks.
  • Fluorescence and photophysical studies: intramolecular hydrogen bonding between the phenol and the carbonyl governs absorption and emission behaviour, so the compound serves as a model system for probing such effects.
  • Cross aldol and Claisen condensation chemistry: the acetyl group remains reactive under standard condensation conditions, allowing chain extension and the assembly of larger conjugated frameworks from a single scaffold.
  • Formation of carbonyl derivatives: reaction with hydroxylamine or hydrazine reagents converts the ketone into oximes or hydrazones, giving access to derivatised intermediates for further heterocyclic or analytical work.

Brand TCI
CAS number 574-19-6
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes available in the standard pack sizes offered for this catalogue item; storage in a tightly closed container away from light and heat
Physical form crystalline solid; soluble in ethanol, methanol, acetone, chloroform, and dimethyl sulfoxide
Storage —
  • Catalogue reference: H0936

Store the material in a tightly closed original container, kept in a cool, dry, and well ventilated area away from direct sunlight, heat sources, and incompatible reagents. Amber glass or the supplier's original packaging is appropriate for limiting light exposure, and containers should be resealed promptly after use to reduce moisture uptake by the crystalline solid. Handle the compound in a fume hood using gloves, safety glasses, and a laboratory coat, avoiding the generation of dust during weighing and transfer. Consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials through established chemical waste channels.

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