2,2'-(2,5-Dimethoxy-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Name: 2,2'-(2,5-Dimethoxy-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
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CAS No. 1338777-82-4
Cat. No. CS-0312297
Purity≥98%
MDL No.None

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2,2'-(2,5-Dimethoxy-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)|CS-0312297

Structure of 1338777-82-4

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General Information

CAS No. 1338777-82-4
Cat. No. CS-0312297
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₃₂B₂O₆
Molecular Weight 390.09
Synonym(s) OC1801, 2,2'-(2,5-Dimethoxy-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
SMILES COC1=C(B2OC(C)(C)C(C)(C)O2)C=C(OC)C(B3OC(C)(C)C(C)(C)O3)=C1

Description

This boronate reagent features a 2,5-dimethoxy-1,4-phenylene core flanked by tetramethyl-1,3,2-dioxaborolane units, enabling efficient Suzuki-Miyaura coupling under mild conditions. The electron-rich aromatic scaffold enhances reactivity while the sterically shielded boronate groups ensure stability and reduced protodeboronation. Ideal for constructing biaryl architectures in complex molecule synthesis.

Application

This boronate ester serves as a versatile bis-aryl building block for Suzuki-Miyaura coupling, enabling efficient construction of biaryl scaffolds with high functional group tolerance. The 2,5-dimethoxy-1,4-phenylene spacer provides enhanced solubility and stability, while the tetramethyl-substituted dioxaborolane moieties ensure excellent bench stability and compatibility with standard cross-coupling conditions. Ideal for iterative synthesis and macrocycle formation 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 : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

TPSA 55.38
LogP 2.3022
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2,2'-(2,5-Dimethoxy-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

CAS No. 1338777-82-4

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