Methyl 3-oxoisoindoline-4-carboxylate

Name: Methyl 3-oxoisoindoline-4-carboxylate
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CAS No. 935269-25-3
Cat. No. CS-0169328
Molecule weight191.18
Purity≥98%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Methyl 3-oxoisoindoline-4-carboxylate|CS-0169328

Structure of 935269-25-3

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General Information

CAS No. 935269-25-3
Cat. No. CS-0169328
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₉NO₃
Molecular Weight 191.18
Synonym(s) 3-Oxo-2,3-Dihydro-1H-Isoindole-4-Carboxylic Acid Methyl Ester
SMILES O=C(C1=CC=CC(CN2)=C1C2=O)OC

Description

Methyl 3-oxoisoindoline-4-carboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring a fused isoindoline core with a ketone at the 3-position and an ester at the 4-position. This scaffold integrates readily into synthetic sequences requiring electron-deficient aromatic systems, enabling efficient access to complex alkaloids and pharmaceutical intermediates through selective functionalization at the carbonyl and olefinic sites.

Application

Methyl 3-oxoisoindoline-4-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to isoindoline scaffolds prevalent in bioactive molecules. The molecule combines a masked amide functionality with a reactive enone system, facilitating nucleophilic additions, conjugate additions, and cyclization reactions under mild conditions. Its bench-stable nature and compatibility with common functional groups simplify purification and scale-up, making it ideal for iterative synthesis campaigns targeting heterocyclic drug candidates.

Synthesis

Route1
- 935269-24-2
- ~52%
- In-stock
  
  935269-25-3
References
- Hughes, Terry V.; Emanuel, Stuart L.; O'Grady, Harold R.; Connolly, Peter J.; Rugg, Catherine; Fuentes-Pesquera, Angel R.; Karnachi, Prabha; Alexander, Richard; Middleton, Steven A. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 18 p. 5130 - 5133

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-P330-P362-P405-P501

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Computational Chemistry Data

TPSA 55.4
LogP 0.7166
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Key Words

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Methyl 3-oxoisoindoline-4-carboxylate

CAS No. 935269-25-3

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