3-Ethoxycarbonylphenylboronic acid
3-Ethoxycarbonylphenylboronic acid (CAS: 4334-87-6) is an organoboron compound with the linear formula C2H5OCOC6H4B(OH)2 and a molecular weight of 193.99 g/mol. This aryl boronic acid derivative is a valuable building block in organic synthesis. It serves as a key reactant in various palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura couplings, and is instrumental in the preparation of complex organic molecules and pharmaceutical intermediates.
- IUPAC
- 3-Carboethoxyphenylboronic acid
- Synonyms
- 3-Carboethoxyphenylboronic acid
Suzuki-Miyaura Coupling Reactions
3-Ethoxycarbonylphenylboronic acid is widely employed as a coupling partner in palladium-catalyzed Suzuki-Miyaura reactions. This enables the formation of new carbon-carbon bonds, crucial for constructing biaryl systems and other complex organic frameworks.
Arylation of Aldehydes
This boronic acid is utilized in palladium-catalyzed arylation of aldehydes. This application facilitates the direct introduction of aryl groups onto aldehyde functionalities, contributing to the synthesis of diverse organic structures.
Reductive Cross-Coupling
The compound finds application in reductive cross-coupling reactions. These processes are important for the synthesis of substituted organic molecules where a reductive step is integrated with the coupling.
Synthesis of Pharmaceutical Intermediates
It serves as a precursor in the preparation of specific pharmaceutical intermediates, such as β3-adrenergic receptor agonists. Its structural features make it suitable for building complex drug molecules.
Transmetalation Reactions
3-Ethoxycarbonylphenylboronic acid participates in transmetalation reactions. This process is a fundamental step in many cross-coupling methodologies, involving the transfer of the organic group from boron to a metal catalyst.
| Molecular weight | 193.99 |
|---|---|
| Linear formula | C2H5OCOC6H4B(OH)2 |
| Application | Reactant for:• Palladium-catalyzed Suzuki-Miyaura coupling1,2• Palladium-catalyzed arylation of aldehydes3• Reductive cross coupling reactions4• Preparation of β3-adrenergic receptor agonist5• Transmetalation reactions6 |
| Melting point | 135-139 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
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-Ethoxycarbonylphenylboronic acid used for?
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3-Ethoxycarbonylphenylboronic acid is primarily used as a reactant in palladium-catalyzed Suzuki-Miyaura coupling reactions, arylation of aldehydes, reductive cross-coupling reactions, and for the preparation of pharmaceutical intermediates. It is also employed in transmetalation reactions.
What is the CAS number and chemical formula for 3-Ethoxycarbonylphenylboronic acid?
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The CAS number is 4334-87-6, and the linear chemical formula is C2H5OCOC6H4B(OH)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this compound for research and chemical synthesis purposes. Please refer to the product specification sheet for current assay and purity details. TSS does not represent this product as USP, BP, or EP grade.
How should 3-Ethoxycarbonylphenylboronic acid be handled safely?
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This compound is a warning hazard. It causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Use appropriate personal protective equipment, including a dust mask (type N95 US), eyeshields, and gloves. Ensure adequate ventilation and avoid breathing dust.
Is 3-Ethoxycarbonylphenylboronic acid a controlled substance?
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Based on the provided data, 3-Ethoxycarbonylphenylboronic acid is not listed as a controlled substance.
How is 3-Ethoxycarbonylphenylboronic acid packaged and shipped?
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Tech Serve Solutions carefully packages and exports chemicals globally, adhering to all necessary regulations for safe transportation. Specific packaging details can be provided upon request.
How can I request a quote or sample of 3-Ethoxycarbonylphenylboronic acid?
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To request a quote or a sample, please use the 'Request a Quote' or 'Sample Request' forms available on the Tech Serve Solutions website, or contact our sales team directly.
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