4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one
Brand: ChemScene
Availability: InStock
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CAS No. 765948-78-5
Cat. No. CS-0051135
Purity≥97%
MDL No.None

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one|CS-0051135

Structure of 765948-78-5

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General Information

CAS No. 765948-78-5
Cat. No. CS-0051135
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BNO₃
Molecular Weight 259.11
Synonym(s) 4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-2,3-dihydroisoindol-1-one
SMILES CC1(C)OB(OC1(C)C)C1=C2CNC(=O)C2=CC=C1

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one features a stable boronate ester integrated with an isoindolin-1-one scaffold, enabling efficient Suzuki-Miyaura coupling. This bench-stable reagent facilitates rapid access to biologically relevant heterocyclic architectures under standard conditions.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its isoindolin-1-one core provides a rigid, electron-deficient scaffold suitable for medicinal chemistry applications. The tetramethyl-substituted dioxaborolane enhances stability and minimizes protodeboronation, enabling reliable coupling under standard conditions. Ideal for late-stage functionalization and diversity-oriented synthesis.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  337536-15-9
- ~61%
- In-stock
  
  765948-78-5
References
- Curtin, Michael L.; Frey, Robin R.; Heyman, H. Robin; Sarris, Kathy A.; Steinman, Douglas H.; Holmes, James H.; Bousquet, Peter F.; Cunha, George A.; Moskey, Maria D.; Ahmed, Asma A.; Pease, Lori J.; Glaser, Keith B.; Stewart, Kent D.; Davidsen, Steven K.; Michaelides, Michael R. Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 17 p. 4505 - 4509
Route2
- In-stock
  
  99548-54-6
- ~%
- In-stock
  
  765948-78-5
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 14, # 17 p. 4505 - 4509
Route3
- 21900-48-1
- ~%
- In-stock
  
  765948-78-5
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 14, # 17 p. 4505 - 4509

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

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Computational Chemistry Data

TPSA 47.56
LogP 1.2292
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

CAS No. 765948-78-5

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