trans-(2-Cyclohexylvinyl)boronic acid
trans-(2-Cyclohexylvinyl)boronic acid (CAS: 37490-33-8; Formula: C8H15BO2; MW: 154.01) is a valuable organoboron compound. It is primarily employed as a reactant in various palladium-catalyzed coupling reactions, including asymmetric Suzuki-Miyaura coupling. This compound is a key building block in organic synthesis, particularly for introducing the cyclohexylvinyl moiety into complex molecules. Its utility extends to chiral synthesis applications, making it indispensable for advanced chemical research and development.
- IUPAC
- (E)-(2-Cyclohexylvinyl)boronic acid,trans-(2-Cyclohexylethenyl)boronic acid
Palladium-Catalyzed Coupling Reactions
This boronic acid serves as an essential reactant in palladium-catalyzed coupling reactions, enabling the formation of carbon-carbon bonds. Its structure is well-suited for these transformations, facilitating complex molecule construction.
Asymmetric Suzuki-Miyaura Coupling
It is a key component in asymmetric Suzuki-Miyaura coupling reactions. This application is crucial for the stereoselective synthesis of chiral compounds, allowing for precise control over molecular stereochemistry.
Chiral Synthesis
The compound participates in chiral palladacycle-catalyzed asymmetric ring-opening reactions. This highlights its importance in the field of enantioselective synthesis and the preparation of stereochemically pure intermediates.
| Molecular weight | 154.01 |
|---|---|
| Empirical formula | C8H15BO2 |
| Assay | 95% |
| Storage temperature | 2-8°C |
| Application | Reactant for:• Pd-catalyzed coupling reactions1• Chiral palladacycle-catalyzed asymmetric ring-opening reaction2• Asymmetric Suzuki-Miyaura coupling3 |
| Melting point | 106-111 °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 trans-(2-Cyclohexylvinyl)boronic acid used for?
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trans-(2-Cyclohexylvinyl)boronic acid is used as a reactant in palladium-catalyzed coupling reactions, including asymmetric Suzuki-Miyaura coupling and chiral palladacycle-catalyzed asymmetric ring-opening reactions.
What is the CAS number and formula for trans-(2-Cyclohexylvinyl)boronic acid?
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The CAS number is 37490-33-8 and the molecular formula is C8H15BO2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies trans-(2-Cyclohexylvinyl)boronic acid with an assay of 95%. TSS does not represent this product as USP, BP, EP, or any other pharmacopoeial grade.
How should trans-(2-Cyclohexylvinyl)boronic acid be handled and stored?
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Handle trans-(2-Cyclohexylvinyl)boronic acid with appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter may be necessary. Store at 2-8°C.
Is trans-(2-Cyclohexylvinyl)boronic acid a hazardous substance?
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trans-(2-Cyclohexylvinyl)boronic acid is classified with a WGK (Germany) of 3, indicating it is a substance that poses a significant risk to water. Appropriate safety precautions must be taken during handling and disposal.
How is this chemical exported and how can I get a quote?
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Tech Serve Solutions globally exports this chemical. For quotes or to request a sample, please contact our sales team directly through our website.
How is trans-(2-Cyclohexylvinyl)boronic acid synthesized?
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Published preparations of trans-(2-Cyclohexylvinyl)boronic acid are documented in the chemical literature and patent records — see the synthesis and sourcing section on this page for reference links. Tech Serve Solutions supplies trans-(2-Cyclohexylvinyl)boronic acid ready to use; request a quote for current grades and pack sizes.
How trans-(2-Cyclohexylvinyl)boronic acid (37490-33-8) is synthesized — and where to buy it
trans-(2-Cyclohexylvinyl)boronic acid is an (E)-alkenylboronic acid for stereodefined Suzuki–Miyaura couplings, installing the trans-cyclohexylvinyl unit in one step.
Published synthesis & references
Why make it?
Alkenylboronic acids protodeboronate on storage — an aged bottle quietly kills coupling yield. We supply a fresh, assay-verified lot with a Certificate of Analysis.
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