1-(Tert-butyl) 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Name: 1-(Tert-butyl) 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate
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CAS No. 942070-38-4
Cat. No. CS-0173847
Purity≥98%
MDL No.None

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1-(Tert-butyl) 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate|CS-0173847

Structure of 942070-38-4

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General Information

CAS No. 942070-38-4
Cat. No. CS-0173847
Purity ≥98%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₇H₂₆BNO₆
Molecular Weight 351.20
Synonym(s) 1-Tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrole-1,2-dicarboxylate
SMILES CC(C)(OC(N1C=C(B2OC(C)(C(C)(O2)C)C)C=C1C(OC)=O)=O)C

Description

This boronate ester integrates a sterically shielded tetramethyl-1,3,2-dioxaborolane moiety with a tert-butyl and methyl-substituted pyrrole scaffold, enabling robust coupling under standard Suzuki-Miyaura conditions. The electron-rich pyrrole core enhances reactivity while the bulky groups confer stability and resistance to protodeboronation.

Application

1-(Tert-butyl) 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylborolane moiety enables efficient palladium-catalyzed coupling with aryl and vinyl halides under mild conditions. Its bench-stable nature, combined with orthogonal functionality and ease of purification, makes it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 25015-63-8
- 294659-30-6
- ~72%
- In-stock
  
  942070-38-4
References
- Kallepalli, Venkata A.; Shi, Feng; Paul, Sulagna; Onyeozili, Edith N.; Maleczka Jr., Robert E.; Smith III, Milton R. Journal of Organic Chemistry, 2009 , vol. 74, # 23 p. 9199 - 9201
Route2
- In-stock
  
  73183-34-3
- 294659-30-6
- ~%
- In-stock
  
  942070-38-4
References
- Angewandte Chemie - International Edition, , vol. 51, # 37 p. 9288 - 9291 Angew. Chem. Int. Ed., , vol. 124, # 37 p. 9422 - 9425,4

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+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 75.99
LogP 2.3571
H_Acceptors 7
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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1-(Tert-butyl) 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

CAS No. 942070-38-4

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