3,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Name: 3,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
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CAS No. 1958113-34-2
Cat. No. CS-0528601
Purity≥97%
MDL No.MFCD32184537

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Type	HazMat Fee
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3,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole|CS-0528601

Structure of 1958113-34-2

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General Information

CAS No. 1958113-34-2
Cat. No. CS-0528601
Purity ≥97%
MDL No. MFCD32184537
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₃₁B₂NO₄
Molecular Weight 419.13
Synonym(s) None
SMILES CC1(C)OB(C2=CC=C3NC4=C(C3=C2)C=C(B5OC(C)(C(C)(C)O5)C)C=C4)OC1(C)C

Description

3,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole features two robust boronate ester groups flanking a planar carbazole core, enabling efficient Suzuki-Miyaura coupling. The tetramethyl-substituted dioxaborolane moieties enhance stability and solubility in organic media. This bifunctional scaffold integrates readily into conjugated polymers and complex molecular architectures under standard conditions.

Application

3,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole serves as a versatile Suzuki-Miyaura coupling building block, enabling efficient construction of carbazole-based biaryls and extended π-conjugated systems. The bis-boronic ester functionality offers excellent stability, mild handling, and broad functional group tolerance, facilitating sequential or site-selective cross-coupling reactions. This reagent is particularly valuable in the synthesis of optoelectronic materials and pharmaceutical scaffolds requiring precise structural control.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 52.71
LogP 3.9195
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Carbazole compounds

Key Words

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3,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

CAS No. 1958113-34-2

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