Methyl (S)-2-(Boc-amino)-4-bromobutyrate

CAS No. 76969-87-4
Cat. No. CS-0154520
Purity≥96%
MDL No.MFCD18207337

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Methyl (S)-2-(Boc-amino)-4-bromobutyrate|CS-0154520

Structure of 76969-87-4

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Description

Methyl (S)-2-(Boc-amino)-4-bromobutyrate features a chiral, bench-stable Boc-protected amino acid building block with a bromine atom at the γ-position. This electrophilic handle enables selective late-stage functionalization in peptide synthesis and diversification of bioactive scaffolds. The ester moiety facilitates efficient coupling reactions under standard conditions, while the sterically hindered Boc group ensures minimal side reactions during manipulation.

Application

Methyl (S)-2-(Boc-amino)-4-bromobutyrate serves as a versatile chiral building block for the synthesis of bioactive molecules and pharmaceutical intermediates. The Boc-protected amine and bromide functionalities enable sequential functionalization via standard coupling, alkylation, and cross-coupling reactions. Its bench-stable nature and compatibility with diverse reaction conditions facilitate efficient access to complex heterocyclic scaffolds and peptide-like architectures in medicinal chemistry workflows.

General Information

CAS No. 76969-87-4
Cat. No. CS-0154520
Purity ≥96%
MDL No. MFCD18207337
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₈BrNO₄
Molecular Weight 296.16
Synonym(s) (S)-4-Bromo-2-(tert-butoxycarbonylamino)butyric acid methyl ester
SMILES CC(C)(OC(N[C@H](C(OC)=O)CCBr)=O)C

Computational Chemistry Data

TPSA 64.63
LogP 1.8377
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 4

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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Methyl (S)-2-(Boc-amino)-4-bromobutyrate

CAS No. 76969-87-4

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