tert-Butyl (5-ethynylpyridin-3-yl)carbamate

Name: tert-Butyl (5-ethynylpyridin-3-yl)carbamate
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CAS No. 1192472-59-5
Cat. No. CS-0134547
Purity≥97%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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tert-Butyl (5-ethynylpyridin-3-yl)carbamate|CS-0134547

Structure of 1192472-59-5

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General Information

CAS No. 1192472-59-5
Cat. No. CS-0134547
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₄N₂O₂
Molecular Weight 218.25
Synonym(s) Carbamic acid, N-(5-ethynyl-3-pyridinyl)-, 1,1-dimethylethyl ester
SMILES O=C(OC(C)(C)C)NC1=CC(C#C)=CN=C1

Description

tert-Butyl (5-ethynylpyridin-3-yl)carbamate features a pyridine ring bearing an ethynyl group at the 5-position and a tert-butyloxycarbonyl-protected amine at the 3-position. This bifunctional scaffold enables efficient coupling in copper-catalyzed click reactions and serves as a stable precursor for bioconjugation and medicinal chemistry applications, where the protected amine can be selectively deprotected under mild conditions.

Application

tert-Butyl (5-ethynylpyridin-3-yl)carbamate serves as a versatile building block for the synthesis of pyridine-based scaffolds, enabling efficient Sonogashira coupling and copper-catalyzed azide–alkyne cycloaddition (CuAAC) reactions. The protected amine and terminal alkyne functionalities offer orthogonal reactivity, facilitating modular construction of complex heterocycles. Its bench-stable nature and ease of purification make it well-suited for iterative synthetic campaigns in medicinal chemistry and process development.

Synthesis

Route1
- 1192472-58-4
- ~68%
- In-stock
  
  1192472-59-5
References
- INCYTE CORPORATION Patent: US2010/190804 A1, 2010 ; Location in patent: Page/Page column 79 ; US 20100190804 A1

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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Computational Chemistry Data

TPSA 51.22
LogP 2.4099
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl (5-ethynylpyridin-3-yl)carbamate

CAS No. 1192472-59-5

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