tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Name: tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate
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CAS No. 212127-83-8
Cat. No. CS-W008634
Molecule weight295.18
Purity≥97%
MDL No.MFCD10697918

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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate|CS-W008634

Structure of 212127-83-8

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General Information

CAS No. 212127-83-8
Cat. No. CS-W008634
Purity ≥97%
MDL No. MFCD10697918
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₆BNO₄
Molecular Weight 295.18
Synonym(s) tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate; tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-2,5-dihydro-1h-pyrrole-1-carboxylate
SMILES O=C(N1CC(B2OC(C)(C)C(C)(C)O2)=CC1)OC(C)(C)C

Description

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate features a stable boronate ester integrated into a dihydropyrrole scaffold, enabling direct coupling in Suzuki-Miyaura reactions. This bench-stable reagent streamlines access to functionalized pyrrole derivatives with minimal handling complexity.

Application

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The dioxaborolane moiety enables efficient coupling with aryl and vinyl halides under mild conditions, while the protected pyrrolidine scaffold offers orthogonal functional group compatibility. Its high stability, ease of handling, and predictable reactivity make it ideal for constructing complex heterocyclic frameworks in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  630121-86-7
- In-stock
  
  73183-34-3
- ~82%
- In-stock
  
  212127-83-8
References
- US2010/204265 A1, ; Page/Page column 91; 92 ;
Route2
- 212127-74-7
- ~83%
- In-stock
  
  212127-83-8
References
- Journal of the American Chemical Society, , vol. 120, # 31 p. 7995 - 7996

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 48
LogP 2.7949
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrroline compounds

Key Words

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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

CAS No. 212127-83-8

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