4-Amino-3-(2,2-dimethoxy-ethyl)-phenol is an aromatic amino acid derivative featuring a phenolic ring with an aniline-type primary amino group and a 2,2-dimethoxy-ethyl substituent at the meta position relative to the phenol. The molecule bears a phenolic hydroxyl and a primary amine, while the side-chain includes an acetal-protected carbon framework that can be used to control polarity and reactivity during synthesis and subsequent functional-group transformations. As a chemically defined building block, it is employed in peptide and small-molecule synthesis and in structure-activity or chemical biology studies where an amino-functional aromatic scaffold with a masked aldehyde-equivalent handle is required for conjugation, labeling, or stepwise assembly of more complex derivatives.
CAT No: CP26864
CAS No:250739-30-1
Synonyms/Alias:TODD-LINKER;250739-30-1;4-amino-3-(2,2-dimethoxyethyl)phenol;4-AMINO-3-(2,2-DIMETHOXY-ETHYL)PHENOL;4-AMINO-3--PHENOL;SCHEMBL1404238;CTK4F4928;ZINC2506584;AKOS006276075;3-(2,2-Dimethoxyethyl)-4-aminophenol;OR049220;OR247960;Phenol,4-amino-3-(2,2-dimethoxyethyl)-;KB-239990;RT-009361
4-Amino-3-(2,2-dimethoxy-ethyl)-phenol is an aromatic amino alcohol-type building block featuring a phenolic hydroxyl and a primary amino group on the ring, alongside a 2,2-dimethoxy-ethyl substituent that is commonly used as a masked carbonyl equivalent for downstream functionalization. This structure makes the compound a practical intermediate for medicinal chemistry and heterocycle/side-chain construction, where the combination of an aniline-like handle and a phenol provides orthogonal reactivity for selective derivatization. In synthetic workflows, the acetal-protected ethyl unit is often retained during early coupling steps and then converted later to access more reactive carbonyl-containing motifs.
1. Medicinal Chemistry Intermediates
4-Amino-3-(2,2-dimethoxy-ethyl)-phenol is widely used in small-molecule discovery chemistry as a versatile intermediate for assembling substituted aromatic scaffolds and introducing a functionalized ethyl side chain. Medicinal chemistry groups and custom synthesis teams leverage the coexistence of a primary amino group and a phenolic hydroxyl to enable sequential derivatization strategies, such as forming amide or urea linkages from the amino functionality while tuning the phenol for further coupling or protection. The 2,2-dimethoxy-ethyl substituent provides a convenient, stable handle during library synthesis, supporting multi-step routes that require a protected carbon framework before final unveiling to a carbonyl-bearing motif.
2. Heterocycle And Ring-Construction
4-Amino-3-(2,2-dimethoxy-ethyl)-phenol serves as a building block for heterocycle synthesis where an aniline/phenol pattern and a masked carbonyl precursor are both advantageous. Research groups developing nitrogen-containing ring systems often use the amino group for cyclization precursor formation, while the phenolic hydroxyl can be used to modulate reactivity and influence chemoselectivity during ring closure steps. The acetal-protected ethyl substituent supports synthetic planning in which the carbon skeleton is introduced early, then converted at a later stage to enable formation of cyclic structures bearing oxygenated substituents.
3. Pharmaceutical Side-Chain Development
4-Amino-3-(2,2-dimethoxy-ethyl)-phenol is employed in pharmaceutical intermediate development to generate analogs with controlled substitution patterns on phenolic aromatic cores. Process and route-development chemists value this reagent for constructing side-chain-bearing aromatic intermediates that can be carried through coupling, protection, and activation steps before final functional group interconversions. The presence of both an amino handle and a phenolic hydroxyl supports flexible downstream transformations, enabling the synthesis of multiple derivative classes from a common intermediate while maintaining a protected ethyl carbon framework during earlier stages of the build.
4. Specialty Organic Synthesis Building Block
4-Amino-3-(2,2-dimethoxy-ethyl)-phenol is also used as a specialty reagent in academic and industrial organic synthesis for preparing substituted phenol-amine derivatives and related functionalized aromatics. Synthetic chemistry laboratories incorporate it when they need a single scaffold that contains two distinct reactive sites on the aromatic ring and a stable acetal-protected substituent for later conversion. This makes the compound useful for constructing research-grade analogs, reference compounds, and intermediate sets used in structure-activity relationship studies, where consistent starting material structure and modular derivatization are important.
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