3-Chloro-4-methoxyphenylboronic acid
3-Chloro-4-methoxyphenylboronic acid (CAS: 175883-60-0) is an organoboron compound with the formula ClC6H3(OCH3)B(OH)2 and a molecular weight of 186.40 g/mol. It serves as a versatile reactant in various catalytic coupling reactions. Key applications include its use in palladium-catalyzed Suzuki and Stille couplings, copper-catalyzed N-arylation, and rhodium-catalyzed annulation reactions, enabling the synthesis of complex organic molecules.
Palladium-Catalyzed Cross-Coupling Reactions
This boronic acid is a valuable substrate in Suzuki and Stille coupling reactions. These palladium-catalyzed processes are fundamental for forming carbon-carbon bonds, crucial in the synthesis of pharmaceuticals and advanced materials.
Catalytic Arylation and Annulation
It participates in rhodium/chiral ligand-catalyzed arylation and Dieckmann-type annulation reactions. These methodologies are employed in constructing intricate molecular architectures with high stereoselectivity.
Oxidative Coupling Reactions
The compound acts as a reactant in iron-catalyzed oxidative coupling with benzene derivatives via homolytic aromatic substitution. It is also used in copper-catalyzed oxidative N-arylation for the formation of C-N bonds.
Synthesis of Bioactive Compounds
3-Chloro-4-methoxyphenylboronic acid is utilized in the preparation of microtubule inhibitors, which are being investigated as potential anticancer agents. This highlights its role in medicinal chemistry research.
| Molecular weight | 186.40 |
|---|---|
| Linear formula | ClC6H3(OCH3)B(OH)2 |
| Application | Reactant for:• Iron-catalyzed oxidative coupling with benzene derivatives through homolytic aromatic substitution1• Preparation of microtubule inhibitors as potential antitumors2• Rhodium/chiral ligand-catalyzed arylation/Dieckmann-type annulation3• Copper-catalyzed oxidative N-arylation4• Suzuki and Stille palladium-catalyzed coupling5• Boron-Heck arylation6 |
| Melting point | 238-242 °C(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 3-Chloro-4-methoxyphenylboronic acid used for?
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3-Chloro-4-methoxyphenylboronic acid is used as a reactant in various catalytic coupling reactions, including palladium-catalyzed Suzuki and Stille couplings, copper-catalyzed oxidative N-arylation, and rhodium-catalyzed arylation/annulation. It is also employed in the synthesis of potential anticancer agents like microtubule inhibitors.
What are the CAS number and molecular formula for 3-Chloro-4-methoxyphenylboronic acid?
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The CAS number is 175883-60-0, and the molecular formula is ClC6H3(OCH3)B(OH)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this compound as a research-grade chemical. The exact purity is not specified in the provided data, and we do not represent it as meeting USP, BP, or EP pharmacopoeia standards.
How should 3-Chloro-4-methoxyphenylboronic acid be handled safely?
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When handling, it is essential to wear eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter should be used. The compound has a WGK Germany rating of 3, indicating it is hazardous to water.
Is this chemical suitable for export and international shipment?
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Yes, Tech Serve Solutions specialises in global supply and export of fine chemicals, pharmaceutical intermediates, and laboratory reagents.
How can I request a sample or obtain a quote for 3-Chloro-4-methoxyphenylboronic acid?
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Please contact our sales team directly via our website or by telephone to request a sample or obtain a quote for 3-Chloro-4-methoxyphenylboronic acid.
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