2-Methoxy-1-naphthaleneboronic acid
2-Methoxy-1-naphthaleneboronic acid (CAS: 104116-17-8), with the molecular formula C11H11BO3 and a molecular weight of 202.01 g/mol, is an organoboron compound. It serves as a valuable building block in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions. Its structure lends itself to the design of complex molecules and ligands for various chemical transformations.
- IUPAC
- (2-Methoxy-1-naphthalenyl)boronic acid,(2-Methoxy-1-naphthyl)boronic acid,1-(2-Methoxynaphthyl)boronic acid
- Synonyms
- (2-Methoxy-1-naphthalenyl)boronic acid(2-Methoxy-1-naphthyl)boronic acid1-(2-Methoxynaphthyl)boronic acid
Ligand Design
This boronic acid is utilised in the design of phosphorus C,P-ligands, contributing to environmentally benign cross-coupling reactions. These ligands are crucial for developing more sustainable synthetic methodologies.
Suzuki-Miyaura Coupling
It acts as a reactant in sterically hindered and stereoselective Suzuki-Miyaura coupling reactions. These palladium-catalyzed processes are key for constructing biaryl compounds with controlled stereochemistry.
N-Arylation Reactions
The compound is employed in copper-catalyzed N-arylation of imidazoles. This application is important for the synthesis of nitrogen-containing heterocycles, which are prevalent in pharmaceuticals.
Deboronation Homocoupling
2-Methoxy-1-naphthaleneboronic acid participates in deboronation homocoupling reactions. This process allows for the formation of symmetrical biaryl systems from boronic acid precursors.
| Molecular weight | 202.01 |
|---|---|
| Empirical formula | C11H11BO3 |
| Application | Reactant for:• Design of phosphorus C,P-ligands for environmentally benign cross-coupling reactions1• Sterically hindered Suzuki-Miyaura coupling2• Palladium-catalyzed cross-coupling reactions3• Deboronation homocoupling reactions4• Copper-catalyzed N-arylation of imidazoles5• Stereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling6 |
| Melting point | 125-130 °C |
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
| Water hazard class (WGK, DE) | 3 |
|---|---|
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26 |
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 2-Methoxy-1-naphthaleneboronic acid used for?
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It is primarily used as a reactant in various cross-coupling reactions, including Suzuki-Miyaura coupling, N-arylation, and in the design of ligands for catalysis. It is a key building block in organic synthesis for creating complex molecules.
What are the CAS number and chemical formula?
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The CAS number for 2-Methoxy-1-naphthaleneboronic acid is 104116-17-8, and its chemical formula is C11H11BO3.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this compound for research and development purposes. The specific assay/grade will be detailed on the Certificate of Analysis. We do not represent this product as USP, BP, or EP grade.
How should 2-Methoxy-1-naphthaleneboronic acid be handled?
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According to GHS information, it is a Warning substance, causing skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Handle with appropriate personal protective equipment, avoiding dust formation and inhalation. Ensure good ventilation.
Is this chemical shipped internationally?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals, and we can arrange for the packing and shipment of 2-Methoxy-1-naphthaleneboronic acid worldwide.
How can I request a quote or sample?
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To request a quote or a sample, please visit the product page on our website and use the 'Request a Quote' or 'Request a Sample' form, providing your contact details and requirements.
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