4-Bromo-3,5-dimethylphenylboronic acid

Name: 4-Bromo-3,5-dimethylphenylboronic acid
Brand: ChemScene
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CAS No. 1451391-45-9
Cat. No. CS-0189824
Purity≥95%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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4-Bromo-3,5-dimethylphenylboronic acid|CS-0189824

Structure of 1451391-45-9

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General Information

CAS No. 1451391-45-9
Cat. No. CS-0189824
Purity ≥95%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₀BBrO₂
Molecular Weight 228.88
Synonym(s) (4-Bromo-3,5-dimethylphenyl)boronic acid
SMILES CC1=C(C(=CC(=C1)B(O)O)C)Br

Description

4-Bromo-3,5-dimethylphenylboronic acid features a sterically hindered boronic acid group flanked by two methyl substituents and a bromine atom, enabling selective cross-coupling in Suzuki-Miyaura reactions. The electron-rich aromatic core enhances reactivity under mild conditions, while the bench-stable nature simplifies handling and storage. This structure facilitates efficient incorporation into complex molecular architectures.

Application

4-Bromo-3,5-dimethylphenylboronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-dimethyl substitution enhances bench stability and reduces protodeboronation, while the bromine handle permits downstream functionalization via cross-coupling or palladium-catalyzed transformations. Ideal for constructing substituted biaryls and heterocyclic scaffolds in medicinal chemistry and materials science.

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

TPSA 40.46
LogP 0.74574
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-3,5-dimethylphenylboronic acid

CAS No. 1451391-45-9

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