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Description
TCI H0189 2'-Hydroxyacetanilide is the ortho isomer of acetaminophen, with the hydroxyl group positioned directly adjacent to the acetamide group on the benzene ring. This close positional relationship creates the possibility of intramolecular hydrogen bonding interactions, which make the compound behave differently from both the meta and para isomers. That distinction makes it a particularly interesting subject of study in chemistry and pharmaceutical laboratories. On the research bench, the compound serves as a structural comparison standard in acetanilide isomer studies, while also functioning as a bifunctional aromatic building block for the synthesis of heterocyclic compounds such as benzoxazoles and other cyclization derivatives that exploit the two neighbouring functional groups.
The characteristic that drives its selection is the proximity of the two functional groups, which opens an efficient route to intramolecular cyclization reactions without requiring rearrangement of the molecular framework. This property is rarely available in the other isomers and is the principal reason synthetic researchers choose the ortho isomer for this class of work. The compound presents as a crystalline solid that is straightforward to weigh out accurately, dissolves in polar organic solvents such as methanol and ethanol, and remains reasonably stable under ordinary laboratory storage conditions. TCI grade material provides the consistency expected of a reference-quality reagent.
In Indonesian laboratories, 2'-Hydroxyacetanilide is typically found in university organic synthesis groups, pharmaceutical research units, and analytical laboratories working on isomer characterization. It supports teaching and research work where the behaviour of ortho-substituted acetanilides must be contrasted against the more familiar para isomer, and it is used in method development where a well-defined bifunctional aromatic starting material is required for building heterocyclic scaffolds.
Laboratory Applications
Benzoxazole synthesis — the adjacent hydroxyl and acetamide groups allow intramolecular cyclization to proceed efficiently, giving direct access to the benzoxazole ring system.
Acetanilide isomer comparison studies — serves as the ortho reference point against meta and para isomers, allowing researchers to correlate substitution position with observed chemical behaviour.
Bifunctional aromatic building block — the two neighbouring reactive handles on one ring permit sequential or cooperative functionalization strategies in multi-step organic synthesis routes.
Intramolecular hydrogen bonding investigations — the ortho arrangement creates a defined internal hydrogen bond, making this compound a clean model system for spectroscopic study.
Pharmaceutical structure-activity research — as the ortho analogue of acetaminophen, it supports comparative studies examining how functional group placement influences molecular properties and behaviour.
Specifications
Brand: TCI (Tokyo Chemical Industry)
CAS Number: 614-80-2
Catalogue Number: H0189
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Physical Form: Crystalline solid, soluble in polar organic solvents such as methanol and ethanol
Storage: Store under normal laboratory conditions in a closed container; pack sizes available on request
Handling and Storage
Store 2'-Hydroxyacetanilide in a tightly closed original container, kept in a cool, dry place away from direct sunlight, moisture, and incompatible chemicals. Amber glass or the supplied manufacturer packaging is suitable for maintaining material integrity over time. Handle the solid in a well-ventilated area or fume hood to avoid inhalation of dust, and wear standard personal protective equipment including safety glasses, gloves, and a laboratory coat. Use clean, dry spatulas when weighing to prevent cross-contamination, and reseal the container promptly after each use. Consult the manufacturer safety data sheet before first use and dispose of residues according to applicable laboratory waste procedures.
