2-(tert-Butoxycarbonyl)isoindoline-5-carboxylic acid

Name: 2-(tert-Butoxycarbonyl)isoindoline-5-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 149353-71-9
Cat. No. CS-0085238
Purity≥95%
MDL No.MFCD08234862

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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2-(tert-Butoxycarbonyl)isoindoline-5-carboxylic acid|CS-0085238

Structure of 149353-71-9

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General Information

CAS No. 149353-71-9
Cat. No. CS-0085238
Purity ≥95%
MDL No. MFCD08234862
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇NO₄
Molecular Weight 263.29
Synonym(s) 2H-Isoindole-2,5-dicarboxylic acid, 1,3-dihydro-, 2-(1,1-dimethylethyl) ester
SMILES O=C(N1CC2=C(C=C(C(O)=O)C=C2)C1)OC(C)(C)C

Description

This boronate moiety integrates seamlessly into Suzuki-Miyaura coupling workflows, offering enhanced stability and ease of handling. The tert-butyl ester group enables selective deprotection under mild acidic conditions, while the isoindoline scaffold provides a rigid, electron-rich platform for downstream functionalization in medicinal chemistry applications.

Application

2-(tert-Butoxycarbonyl)isoindoline-5-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of isoindoline-based scaffolds through mild deprotection and subsequent functionalization. The Boc group provides excellent bench stability and facilitates straightforward purification, while the carboxylic acid functionality supports coupling reactions with amines and amine derivatives under standard conditions. Its well-defined reactivity profile makes it ideal for constructing complex heterocyclic frameworks relevant to API development.

Synthesis

Route1
- 1203600-37-6
- ~99%
- In-stock
  
  149353-71-9
References
- Ajinomoto Co., Inc. Patent: EP2311810 A1, 2011 ; Location in patent: Page/Page column 25 ;
Route2
- 368441-44-5
- ~%
- In-stock
  
  149353-71-9
References
- GLAXO GROUP LIMITED Patent: WO2004/37788 A1, 2004 ; Location in patent: Page 15 ; WO 2004/037788 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

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Computational Chemistry Data

TPSA 66.84
LogP 2.6355
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Key Words

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2-(tert-Butoxycarbonyl)isoindoline-5-carboxylic acid

CAS No. 149353-71-9

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