tert-Butyl 6-chloro-3-formylpyridin-2-ylcarbamate

Name: tert-Butyl 6-chloro-3-formylpyridin-2-ylcarbamate
Brand: ChemScene
Availability: InStock
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CAS No. 294659-72-6
Cat. No. CS-0187981
Purity≥95%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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tert-Butyl 6-chloro-3-formylpyridin-2-ylcarbamate|CS-0187981

Structure of 294659-72-6

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General Information

CAS No. 294659-72-6
Cat. No. CS-0187981
Purity ≥95%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₃ClN₂O₃
Molecular Weight 256.69
Synonym(s) tert-butyl N-(6-chloro-3-formylpyridin-2-yl)carbamate
SMILES CC(C)(C)OC(=O)NC1=C(C=CC(=N1)Cl)C=O

Description

tert-Butyl 6-chloro-3-formylpyridin-2-ylcarbamate features a pyridine scaffold with orthogonal functional handles: a formyl group at C3 enables chemoselective transformations, while the 6-chloro substituent supports late-stage diversification via cross-coupling. The tert-butyl carbamate protects the amine under standard conditions and facilitates deprotection in mild acidic environments. This combination delivers a versatile intermediate for medicinal chemistry campaigns requiring precise structural tuning.

Application

tert-Butyl 6-chloro-3-formylpyridin-2-ylcarbamate serves as a versatile building block for the synthesis of functionalized pyridine scaffolds, enabling efficient access to medicinally relevant heterocycles. The formyl group facilitates nucleophilic additions and condensation reactions, while the chloro and carbamate functionalities offer orthogonal handles for further derivatization. Its bench-stable nature and compatibility with standard coupling and protection strategies make it well-suited for iterative synthetic workflows in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  159603-71-1
- 68-12-2
- ~10%
- In-stock
  
  294659-72-6
References
- Luk, Kin-Chun Patent: US2012/184562 A1, 2012 ; Location in patent: Page/Page column 8; 35 ; US 20120184562 A1
Route2
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  294659-72-6
References
- Journal of Medicinal Chemistry, , vol. 43, # 16 p. 3134 - 3147
Route3
- In-stock
  
  45644-21-1
- ~%
- In-stock
  
  294659-72-6
References
- Journal of Medicinal Chemistry, , vol. 43, # 16 p. 3134 - 3147

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-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 68.29
LogP 2.8945
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl 6-chloro-3-formylpyridin-2-ylcarbamate

CAS No. 294659-72-6

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