1-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole

Name: 1-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole
Brand: ChemScene
Availability: InStock
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CAS No. 953040-54-5
Cat. No. CS-0052451
Purity≥97%
MDL No.None

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1-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole|CS-0052451

Structure of 953040-54-5

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General Information

CAS No. 953040-54-5
Cat. No. CS-0052451
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₈BNO₂
Molecular Weight 207.08
Synonym(s) N-Methylpyrrole-3-boronic acid pinacol ester
SMILES CN1C=CC(=C1)B1OC(C)(C)C(C)(C)O1

Description

1-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole is a bench-stable boronate ester featuring a pyrrolic core with enhanced solubility and reactivity in Suzuki-Miyaura coupling reactions. The tetramethylboronate moiety enables efficient palladium-catalyzed cross-coupling under mild conditions, while the methyl substitution improves stability and handling. This compound integrates readily into complex molecular architectures with minimal purification requirements.

Application

1-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables efficient coupling with aryl and heteroaryl halides under mild conditions, offering excellent functional group tolerance and bench stability. Its pyrrolyl core provides a platform for constructing biologically relevant heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 96-54-8
- In-stock
  
  76-09-5
- In-stock
  
  55718-76-8
- ~0%
- In-stock
  
  953040-54-5
- In-stock
  
  850567-47-4
- 1278579-60-4
References
- THE UNIVERSITY OF MANCHESTER; INGLESON, Michael James Patent: WO2012/25760 A1, 2012 ; Location in patent: Page/Page column 56-57 ;
Route2
- 96-54-8
- In-stock
  
  76-09-5
- ~52%
- In-stock
  
  953040-54-5
- In-stock
  
  850567-47-4
References
- Angewandte Chemie - International Edition, , vol. 50, # 9 p. 2102 - 2106
Route3
- 96-54-8
- ~%
- In-stock
  
  953040-54-5
References
- Journal of the American Chemical Society, , vol. 135, # 1 p. 474 - 487

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 : H317-H319
Precautionary Statements : P261-P264-P272-P280-P302+P352-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 23.39
LogP 1.3243
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

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1-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole

CAS No. 953040-54-5

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