Benzyl prop-2-yn-1-ylcarbamate

Name: Benzyl prop-2-yn-1-ylcarbamate
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CAS No. 120539-91-5
Cat. No. CS-0187319
Purity≥98%
MDL No.None

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Benzyl prop-2-yn-1-ylcarbamate|CS-0187319

Structure of 120539-91-5

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General Information

CAS No. 120539-91-5
Cat. No. CS-0187319
Purity ≥98%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₁NO₂
Molecular Weight 189.21
Synonym(s) N-Cbz-propargylamine
SMILES C#CCNC(OCC1=CC=CC=C1)=O

Description

Benzyl prop-2-yn-1-ylcarbamate serves as a robust protecting group for primary amines, combining the stability of the benzyl moiety with the cleavability of the propargyl carbamate linkage. This reagent enables efficient orthogonal protection in multistep synthesis, particularly valuable in peptide and small-molecule drug development where selective deprotection is critical.

Application

Benzyl prop-2-yn-1-ylcarbamate serves as a robust, bench-stable carbamate protecting group for amines, enabling selective N-alkylation and orthogonal deprotection under mild conditions. Its propargylic carbamate functionality facilitates efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) for click chemistry applications. The molecule exhibits excellent functional group tolerance and simplifies purification in complex synthetic sequences, making it a practical choice for peptide modification and heterocycle synthesis.

Synthesis

Route1
- 501-53-1
- 2450-71-7
- ~99%
- In-stock
  
  120539-91-5
References
- Chemistry - A European Journal, , vol. 17, # 28 p. 7764 - 7767
Route2
- 1885-14-9
- 2450-71-7
- ~%
- In-stock
  
  120539-91-5
References
- US6498172 B1, ;
Route3
- In-stock
  
  13139-17-8
- 2450-71-7
- ~91%
- In-stock
  
  120539-91-5
References
- Synthesis, , # 3 p. 276 - 284

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
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 1.546
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Alkyne

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Terminal Alkynes

Chemical Biology Conjugation Chemistry/Click Chemistry Terminal Alkynes

Key Words

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Benzyl prop-2-yn-1-ylcarbamate

CAS No. 120539-91-5

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