(S)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Name: (S)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate
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CAS No. 1007882-12-3
Cat. No. CS-0006836
Purity≥98%
MDL No.MFCD20527700

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(S)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate|CS-0006836

Structure of 1007882-12-3

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General Information

CAS No. 1007882-12-3
Cat. No. CS-0006836
Purity ≥98%
MDL No. MFCD20527700
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₃₄BN₃O₄
Molecular Weight 439.36
Synonym(s) tert-butyl(S)-2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate
SMILES O=C(N1[C@H](C2=NC=C(C3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)N2)CCC1)OC(C)(C)C

Description

(S)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate is a boronate-functionalized heterocyclic building block featuring a chiral pyrrolidine scaffold. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura coupling workflows, enabling efficient C–C bond formation under mild conditions. The para-boronated aryl group pairs effectively with diverse halogenated partners, while the imidazole moiety enhances regiochemical control in transition metal-catalyzed transformations.

Application

(S)-tert-Butyl 2-(5-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The imidazole-pyrrolidine scaffold provides a rigid, polar pharmacophore core with enhanced solubility and metabolic stability. The diborolane moiety enables efficient coupling under mild conditions, while the tert-butyl carbamate group offers excellent bench stability and straightforward deprotection. This compound facilitates rapid assembly of complex heterocyclic architectures in medicinal chemistry and materials science applications.

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

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Computational Chemistry Data

TPSA 76.68
LogP 4.4479
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(S)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

CAS No. 1007882-12-3

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