2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Name: 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 166591-85-1
Cat. No. CS-W003490
Purity≥98%
MDL No.MFCD08274995

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FedEx Limited Quantities Ground	$0.00
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2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid|CS-W003490

Structure of 166591-85-1

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Description

This tetrahydroisoquinoline derivative features a tert-butoxycarbonyl-protected amine and a carboxylic acid group, enabling direct incorporation into peptide synthesis workflows. The protected nitrogen facilitates efficient coupling reactions, while the electron-rich aromatic core supports diverse functionalization. Bench-stable under standard conditions, it serves as a key building block for bioactive alkaloid analogs and pharmaceutical intermediates.

Application

This compound serves as a versatile building block for the synthesis of isoquinoline-based scaffolds in medicinal chemistry. The tert-butyl carbamate (Boc) group provides excellent stability and orthogonal protection, enabling selective deprotection under mild acidic conditions. The carboxylic acid functionality facilitates direct coupling reactions or derivatization, while the tetrahydroisoquinoline core offers a rigid, pharmacophoric framework relevant to bioactive molecule development. Its bench-stable nature and compatibility with standard peptide and heterocyclic synthesis protocols make it ideal for iterative synthetic workflows.

General Information

CAS No. 166591-85-1
Cat. No. CS-W003490
Purity ≥98%
MDL No. MFCD08274995
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₉NO₄
Molecular Weight 277.32
Synonym(s) 2-N-Boc-1,2,3,4-Tetrahydro-Isoquinoline-1-Carboxylic Acid
SMILES CC(C)(OC(N1CCC2=CC=CC=C2C1C(O)=O)=O)C

Computational Chemistry Data

TPSA 66.84
LogP 2.6055
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Safety Information

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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

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Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroisoquinoline compounds

Key Words

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2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

CAS No. 166591-85-1

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