N-1-Boc-1,2-diaminoethane · HCl

N-1-Boc-1,2-diaminoethane · HCl contains a protected diaminoethane backbone in which one terminal amino group is carbamated with a tert-butoxycarbonyl (Boc) group, while the other amino group remains free as a primary amine and is present as a hydrochloride salt. The molecule therefore bears a Boc-protected nitrogen, a protonated amine chloride counterion, and no carboxyl functional group, making it a diamine building block rather than a free amino acid. As a protected amino-functional intermediate, it is used in stepwise synthesis and peptide or peptidomimetic assembly strategies that require controlled chemoselectivity for coupling at the unprotected amine while the Boc group suppresses undesired side reactions.

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

CAT No: CP27226

CAS No:57260-73-8

Synonyms/Alias:BOC-TRP-OBZL;57229-67-1;CHEMBL429395;2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionicacidbenzylester;SCHEMBL16464197;CTK7G8929;CEMCPAAFDOVLDW-FQEVSTJZSA-N;Nalpha-Boc-tryptophanbenzylester;BOC-L-TRYPTOPHANBENZYLESTER;ZINC2556565;6456AH;BDBM50030139;KM0079;N-|A-Boc-L-Tryptophanbenzylester;AKOS025289392;AM82287;AK170118;L-Tryptophan,N-[(1,1-dimethylethoxy)carbonyl]-,phenylmethylester;(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionicacidbenzylester

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M.F/Formula
C23H26N2O4
M.W/Mr.
196.68
Purity
97%min

N-1-Boc-1,2-diaminoethane · HCl is a protected diamine hydrochloride in which a Boc carbamate masks one primary amine while the second amino group remains available as a protonated chloride salt. The molecule contains an ethane backbone with two nitrogen atoms, providing orthogonal functional-group handles for selective derivatization and subsequent coupling chemistry. The Boc group is acid-labile and can be removed under controlled deprotection conditions to regenerate a free amine for stepwise synthesis, while the salt form improves handling and can influence solubility for downstream transformations. As a chiral-independent but stereochemically relevant building block for amine topology, it functions as a practical intermediate for constructing polyamine motifs, protected diamines, and amino-functional linkers used in peptide and medicinal chemistry workflows.

1. Protected Diamine Synthesis

N-1-Boc-1,2-diaminoethane · HCl supports protected amino building strategies in synthetic organic chemistry by combining an acid-labile Boc carbamate with a second amine that can be selectively functionalized after salt formation. The Boc-protected nitrogen provides a stable handle during carbonyl activation, alkylation, or amide-forming steps, while the remaining amino group enables attachment to acyl chlorides, activated esters, or electrophilic linkers. The hydrochloride counterion can help maintain the amine in a reactive, protonated state for controlled nucleophilic substitution and for managing reactivity during multi-step sequences. Downstream, the compound can be converted into N-Boc diamine derivatives, aminoethyl-containing intermediates, and orthogonally protected polyamine fragments used for fine chemical synthesis and intermediate preparation.

2. Peptide Coupling Building Block

N-1-Boc-1,2-diaminoethane · HCl can be applied to peptide and peptidomimetic construction where an aminoethyl unit is required as a spacer, side-chain surrogate, or backbone extension. The Boc carbamate enables compatibility with peptide coupling conditions by protecting one amine from undesired cross-linking, while the free amino group can participate in amide bond formation or in the synthesis of N-terminal or side-chain functionalized residues. Controlled deprotection of the Boc group can expose an additional amine for subsequent coupling cycles, supporting iterative assembly of diamine-containing peptide analogs. The resulting products can serve as intermediates for incorporating aminoethyl linkers into bioactive peptide scaffolds, enabling structure-activity relationship studies that probe linker length and amine presentation.

3. Bioconjugation Linker Chemistry

N-1-Boc-1,2-diaminoethane · HCl is suitable for chemical biology workflows that require amine-reactive linker installation for biomolecule labeling and conjugation. The orthogonal Boc-protected amine and the second primary amine provide two-stage control over functional-group availability, allowing pre-functionalization of one nitrogen and later exposure of the other for conjugation to activated biomolecule derivatives. The hydrochloride salt form can improve handling of the free amine during coupling to NHS esters, isothiocyanates, aldehyde-derived imines, or other electrophiles used to connect small molecules to proteins and nucleic acids. Downstream, diamine-based linkers prepared from this intermediate can be used to generate conjugates for assay development, biomolecule modification, and analytical reagent synthesis.

4. Process Chemistry Intermediate

N-1-Boc-1,2-diaminoethane · HCl serves as a process-relevant intermediate for industrial chemical manufacturing routes that require orthogonally protected diamines and amine-functional building blocks. The Boc group provides a predictable protection strategy that can be introduced early and removed when needed, supporting scalable stepwise synthesis of aminoethyl derivatives without uncontrolled amine scrambling. The hydrochloride salt form can facilitate consistent feed handling and can help manage solubility and reactivity in manufacturing-scale operations where amine volatility and handling are practical concerns. The compound can be employed to produce protected aminoethyl intermediates for specialty chemical production, including polymer-reactive amines, amine-functional linkers, and downstream fine-chemical intermediates.

5. Polymer And Materials Functionalization

N-1-Boc-1,2-diaminoethane · HCl can be used in functional materials and polymer modification chemistry where diamine functionality enables network formation, surface functionalization, or crosslinker design. The protected amine allows controlled incorporation into polymer backbones or side chains while limiting side reactions during processing, and subsequent Boc deprotection can generate reactive primary amines for further coupling to carboxyl, epoxy, or activated carbonate functionalities. The ethane diamine motif supports formation of amide, urea, or substituted amine linkages that can tune charge density and binding interactions in material surfaces. Downstream, this intermediate can contribute to preparing amino-functional coatings, adsorption media, and polymer-bound reagents used in applied chemical manufacturing and industrial materials development.

Size
1 g;5 g;
InChI
1S/C23H26N2O4/c1-23(2,3)29-22(27)25-20(21(26)28-15-16-9-5-4-6-10-16)13-17-14-24-19-12-8-7-11-18(17)19/h4-12,14,20,24H,13,15H2,1-3H3,(H,25,27)/t20-/m0/s1
InChI Key
CEMCPAAFDOVLDW-FQEVSTJZSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)OCC3=CC=CC=C3

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