4-Hydroxymethyl-phenoxyacetic acid contains a phenoxyacetic acid core bearing a para-hydroxymethyl substituent, classifying it as an aromatic, non-proteinogenic amino-acid-like derivative with a carboxylic acid functional group and a benzylic hydroxymethyl group. The molecule presents an ether-linked phenyl ring system that bears a hydroxymethyl substituent, enabling hydrogen-bonding and providing a chemically addressable alcohol handle while retaining the carboxyl group for salt formation, esterification, or coupling chemistry. In synthetic chemistry and chemical biology workflows, it is employed as a precursor for building more complex aromatic acetic acid derivatives and as a functionalized scaffold for preparing conjugates, linkers, or peptide/biomolecule attachment reagents through carboxyl-group derivatization.
CAT No: CP27363
CAS No:68858-21-9
Synonyms/Alias:4-(Hydroxymethyl)phenoxyaceticacid;68858-21-9;hmplinker;4-Hydroxymethylphenoxyaceticacid;2-[4-(hydroxymethyl)phenoxy]aceticacid;2-(4-(Hydroxymethyl)phenoxy)aceticacid;p-(Hydroxymethyl)phenoxyaceticacid;MFCD00057827;SBB059335;4-Hmpaa;4-phenoxyaceticacid;HMPA-LINKER;HMPAODER;HPALINKER;PubChem11987;AC1L4XYM;AC1Q5WQD;ACMC-1B2RE;Oprea1_767209;KSC489O6N;55730_ALDRICH;H2515_SIGMA;SCHEMBL166364;55730_FLUKA;CTK3I9766
4-Hydroxymethyl-phenoxyacetic acid is an aromatic ether-containing amino acid derivative featuring a phenoxyacetic acid motif and a hydroxymethyl substituent on the aromatic ring. Its combination of a carboxylic acid with a benzylic alcohol makes it a practical building block for medicinal chemistry and materials-oriented organic synthesis, where stable, non-amino functional groups are required for downstream coupling, derivatization, or polymer/bioconjugation precursor design. Researchers select this scaffold to introduce an ether-linked acetic acid handle alongside a reactive alcohol for controlled functional-group transformation during lead optimization and specialty chemical manufacturing.
1. Medicinal Chemistry Intermediates
4-Hydroxymethyl-phenoxyacetic acid is used as a medicinal chemistry intermediate to assemble ether-linked carboxylic acid fragments that appear in structure-activity relationship (SAR) campaigns. Medicinal chemistry groups often rely on this scaffold to generate analog libraries where the phenoxyacetic acid portion provides a recognizable pharmacophore-like motif, while the aromatic hydroxymethyl group offers a convenient point for further derivatization into protected alcohols, ester/amide variants, or other oxygen-functional substituents. The presence of a free carboxylic acid also supports straightforward downstream coupling chemistry in small-molecule synthesis workflows, including preparation of activated derivatives for fragment linking.
2. Polymer And Surface Functionalization
4-Hydroxymethyl-phenoxyacetic acid is applied in materials research as a functional monomer or precursor for polymer and surface modification strategies that require both an acid functionality and a benzylic alcohol. Polymer chemists commonly convert the carboxylic acid into reactive derivatives (for example, for incorporation into polymer backbones or for post-polymer functionalization) while using the hydroxymethyl group as a handle for controlled grafting, crosslinking precursor formation, or attachment of secondary functional groups. This dual-functional design is particularly useful when building materials that need stable aromatic ether linkages and tunable hydrophilicity derived from the oxygen-containing substituents.
3. Bioconjugation Precursor Chemistry
4-Hydroxymethyl-phenoxyacetic acid is frequently used as a bioconjugation precursor in chemical biology workflows where an aromatic ether-linked acid scaffold is needed to introduce a stable linker region into larger constructs. Researchers can transform the carboxylic acid into coupling-ready intermediates to connect to amine- or hydroxyl-reactive partners, while the hydroxymethyl group provides an additional functionalization site for generating conjugates with defined attachment points. This makes the compound useful for preparing linker-bearing reagents used in labeling, immobilization, and probe construction, especially when a non-peptidic, oxygen-rich aromatic spacer is desired for chemical stability in conjugate assemblies.
4. Chiral Building Block Derivatization
4-Hydroxymethyl-phenoxyacetic acid serves as a practical starting scaffold for making chiral or stereodefined derivatives when asymmetric derivatization or resolution-compatible functional forms are required. In specialty chemical development, the free carboxylic acid and hydroxymethyl alcohol can be converted into protected or activated derivatives that support downstream stereochemical control, enabling preparation of enantiomerically enriched analogs for method development, reference material generation, or SAR follow-up. This application is especially relevant when a rigid aromatic ether framework is preferred to reduce conformational variability while still offering two orthogonally transformable functional groups for targeted derivative synthesis.
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