4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid is a substituted aromatic ether amino acid derivative featuring a phenoxybutanoic acid backbone with an additional 1-hydroxyethyl substituent on the aromatic ring system, placing it in the category of non-proteinogenic, structurally modified amino acid analogues. The molecule contains a carboxylic acid functional group and an ether-linked aromatic framework with a nitro group and a methoxy group, providing distinct electronic and hydrogen-bonding characteristics while the side-chain hydroxyl can participate in intermolecular hydrogen bonding; stereochemistry is not specified in the name. In research and synthetic chemistry contexts, this compound is used as a defined building block for preparing further functionalized aromatic ether derivatives and as a substrate-like reagent for structure-activity studies, chemical labeling strategies, or the synthesis of more complex conjugates where the nitro and hydroxyl functionalities offer handles for downstream derivatization.
CAT No: CP26528
CAS No:175281-76-2
Synonyms/Alias:4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitro-phenoxy)butyric acid;
4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid is an aromatic, nitro-substituted phenoxybutanoic acid bearing a secondary hydroxyethyl substituent. Its structure combines a carboxylic acid for further derivatization with phenoxy and nitro functionality that make it useful as a specialized small-molecule building block in chemical biology and medicinal chemistry workflows. Researchers typically leverage this compound as a functionalized amino-acid-like intermediate for constructing conjugates, analog libraries, and linker-bearing derivatives where the phenoxybutanoate motif and hydroxyl handle are key to downstream coupling or property tuning.
1. Medicinal Chemistry Intermediates
4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid is used by medicinal chemistry groups to prepare analogs and side-chain variants for structure-activity relationship studies. The carboxylic acid enables straightforward conversion into activated derivatives for amide or ester formation, supporting the rapid assembly of compound series where the phenoxybutanoate scaffold and the nitro-substituted aromatic ring are retained as pharmacophore-defining elements. The secondary hydroxyethyl group provides an additional functional handle for tuning polarity and hydrogen-bonding characteristics during lead optimization and SAR mapping.
2. Chemical Biology Conjugate Building
4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid is applied as a linker-bearing building block for chemical biology conjugation strategies that require an amino-acid-like carboxyl group for stable attachment to biomolecule-derived scaffolds. Teams in probe development and glycoconjugate or polymer conjugation workflows use the phenoxybutanoic acid motif to introduce a defined aromatic fragment while maintaining a reactive carboxyl functionality for coupling to amines or alcohol-containing partners. The presence of the hydroxyethyl substituent supports downstream derivatization steps that can improve solubility or enable orthogonal functionalization routes in multi-component labeling schemes.
3. Materials And Surface Functionalization
4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid is leveraged in biomaterials and specialty materials research where carboxyl-bearing aromatic intermediates are needed to incorporate defined organic moieties into polymer backbones or surface coatings. The molecule's carboxylic acid supports attachment to material platforms through standard coupling chemistries, while the phenoxy and nitro-substituted aromatic region provides a stable, rigid aromatic contribution that can influence surface chemistry and material compatibility. Researchers also value the hydroxyl-bearing side chain for modulating hydrophilicity and for enabling secondary functionalization when building layered or composite materials.
4. Analytical Reference Derivatives
4-(4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid is used by analytical chemistry teams to generate reference derivatives for method development and characterization of related compound families. In LC-MS and related workflows, the defined aromatic and nitro features help distinguish this scaffold from structurally similar intermediates, supporting targeted identification and impurity profiling during synthesis optimization. Laboratories commonly prepare carboxyl-activated or derivatized forms from this compound to create consistent standards for monitoring conversion, assessing batch-to-batch consistency, and verifying identity of downstream conjugates or analogs.
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