5-BzlO-ICA-OEt

5-BzlO-ICA-OEt contains an amino acid-derived scaffold bearing a benzyl oxy substituent at the 5-position (BzlO) and an ethyl ester at the carboxyl terminus (OEt), placing it in the class of derivatized amino acid esters rather than a free amino acid. The molecule features a free amino functionality paired with a masked carboxyl group as an ethyl ester, and the benzyl-protected oxygen substituent provides an ether handle that can be retained or selectively modified during synthetic sequences. 5-BzlO-ICA-OEt is used as a protected/derivatized amino acid building block for preparing more complex amino acid and peptide derivatives in solution-phase or solid-phase workflows, where the ester and benzyl oxy substituent help control chemoselectivity and provide functional-group compatibility for stepwise assembly and downstream transformations.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25808

CAS No:37033-95-7

Synonyms/Alias:Ethyl5-(benzyloxy)-1H-indole-2-carboxylate;37033-95-7;Ethyl5-benzyloxyindole-2-carboxylate;5-Benzyloxy-2-carbethoxyindole;Ethyl5-(benzyloxy)indole-2-carboxylate;5-Benzyloxyindole-2-carboxylicacidethylester;DCIFXYFKVKDOLL-UHFFFAOYSA-N;SBB048921;5-(Phenylmethoxy)-1H-indole-2-carboxylicacidethylester;ethyl5-(phenylmethoxy)indole-2-carboxylate;NSC30931;AC1L3UYI;Maybridge1_002130;ACMC-209xa3;AC1Q64WS;B1126_ALDRICH;Oprea1_318854;B1126_SIGMA;SCHEMBL710398;CTK3J5839;HMS547I18;ZINC78411;MolPort-000-141-961;ACT02527;ALBB-007608

Chemical Name:5-Benzyloxyindole-2-carboxylic acid ethyl ester, 98%

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M.F/Formula
C18H17NO3
M.W/Mr.
295,34 g/mole

5-BzlO-ICA-OEt is an amino acid derivative featuring an esterified carboxylate (OEt) and a benzyl-protected oxygen substituent (BzlO) on a substituted amino acid framework, making it a practical, isolable intermediate for downstream functionalization and coupling chemistry. Its protected oxygen functionality and ester form help control reactivity during multi-step synthesis, while the amino acid backbone supports use as a building block in peptide-related and medicinal chemistry workflows where selective deprotection or conversion to an activated acid form is required.

1. Pharmaceutical Intermediate Synthesis

5-BzlO-ICA-OEt is used by medicinal chemistry and process development teams as a protected amino acid intermediate for assembling more complex heterocycles, side-chain elaborations, and late-stage functionalization sequences. The benzyl-protected oxygen and esterified carboxylate provide synthetic handle stability during transformations that would otherwise risk uncontrolled hydrolysis or side reactions. In practice, it supports workflows where the derivative must be carried through several steps before conversion to a more reactive acid or coupling-ready form for incorporation into larger candidate structures.

2. Peptide Building Block Development

5-BzlO-ICA-OEt serves as a protected amino acid building block for generating modified peptide segments and peptide-like scaffolds in custom peptide synthesis and peptide chemistry R&D. The protected oxygen substituent helps maintain chemoselectivity during segment assembly, while the ester functionality provides a controlled carboxylate state for subsequent activation or conversion to the corresponding coupling partner. Researchers commonly choose this type of protected derivative when they need to preserve sensitive side-chain functionality until the appropriate stage of peptide coupling or post-coupling derivatization.

3. Protected Side-Chain Functionalization

5-BzlO-ICA-OEt is applied in synthetic chemistry programs that require selective introduction of oxygen-containing substituents under protection to minimize competing reactions. The benzyl-protected oxygen group is particularly useful when the target synthesis demands a protected intermediate that can later be unmasked or transformed to reveal a reactive hydroxyl (or related functionality) at a defined step. This makes the derivative a practical starting material for creating structure-function analogs, tuning polar surface properties, or preparing side-chain variants used in SAR studies and chemical biology probe optimization.

4. Analytical Reference Intermediate Preparation

5-BzlO-ICA-OEt is also used in analytical method development and reference material preparation for LC-based characterization of amino acid derivatives and protected intermediates. Because it is an isolable, structurally defined compound with controlled functional-group protection, it can serve as a practical standard for monitoring reaction progress, assessing intermediate identity, and supporting impurity profiling during multi-step synthesis. Laboratories working on process analytics and synthetic route scouting often rely on such protected derivatives to build robust analytical workflows that distinguish closely related protected forms and ester/acid interconversions.

Size
100 g;
InChI
1S/C18H17NO3/c1-2-21-18(20)17-11-14-10-15(8-9-16(14)19-17)22-12-13-6-4-3-5-7-13/h3-11,19H,2,12H2,1H3
InChI Key
DCIFXYFKVKDOLL-UHFFFAOYSA-N
Canonical SMILES
CCOC(=O)C1=CC2=C(N1)C=CC(=C2)OCC3=CC=CC=C3

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