4-Bromo-2,6-dimethylphenylboronic acid

Name: 4-Bromo-2,6-dimethylphenylboronic acid
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1160561-24-9
Cat. No. CS-0189945
Purity≥98%
MDL No.MFCD13181651

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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4-Bromo-2,6-dimethylphenylboronic acid|CS-0189945

Structure of 1160561-24-9

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General Information

CAS No. 1160561-24-9
Cat. No. CS-0189945
Purity ≥98%
MDL No. MFCD13181651
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₀BBrO₂
Molecular Weight None
Synonym(s) (4-BroMo-2,6-diMethylphenyl)boronic acid
SMILES CC1=C(C(=CC(=C1)Br)C)B(O)O

Description

4-Bromo-2,6-dimethylphenylboronic acid features a sterically hindered boronate moiety flanked by two methyl groups, enhancing stability and reducing protodeboronation. This bench-stable reagent facilitates efficient Suzuki-Miyaura coupling under standard conditions, delivering arylated products with high functional group tolerance.

Application

4-Bromo-2,6-dimethylphenylboronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-methyl groups enhance stability and reduce protodeboronation, while the bromine substituent allows for downstream functionalization via cross-coupling or palladium-catalyzed transformations. Ideal for constructing substituted biaryls and complex heterocycles in medicinal chemistry and materials science workflows.

Synthesis

Route1
- 121-43-7
- In-stock
  
  206559-43-5
- ~%
- In-stock
  
  1160561-24-9
References
- SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG Patent: WO2009/74314 A1, 2009 ; Location in patent: Page/Page column 169 ;

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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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-2,6-dimethylphenylboronic acid

CAS No. 1160561-24-9

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