2-Cyanophenylboronic acid
2-Cyanophenylboronic acid (CAS: 138642-62-3), with the molecular formula NCC<sub>6</sub>H<sub>4</sub>B(OH)<sub>2</sub> and a molecular weight of 146.94 g/mol, is a valuable aryl boronic acid derivative. It serves as a key building block in organic synthesis, particularly in metal-catalyzed reactions. Its primary documented application involves rhodium-catalyzed annulation with alkynes for the synthesis of substituted indenones, highlighting its utility in constructing complex organic frameworks.
- IUPAC
- 2-Cyanobenzeneboronic acid,[m-Cyanophenyl-4-yl]boronic acid
- Synonyms
- 2-Cyanobenzeneboronic acid[m-Cyanophenyl-4-yl]boronic acid
Organic Synthesis Intermediate
2-Cyanophenylboronic acid is employed as a versatile intermediate in organic synthesis. Its structure facilitates participation in various coupling reactions and cyclisation processes.
Rh-Catalyzed Annulation Reactions
This compound is specifically utilised in rhodium-catalyzed [3+2] annulation reactions with alkynes. This methodology efficiently yields substituted indenones, demonstrating its utility in constructing heterocyclic and polycyclic structures.
Synthesis of Complex Molecules
The reactivity profile of 2-Cyanophenylboronic acid makes it suitable for the construction of more intricate molecular architectures, finding use in both academic research and industrial process development.
| Molecular weight | 146.94 |
|---|---|
| Linear formula | NCC6H4B(OH)2 |
| Assay | ≥95.0% |
| Application | Employed in a rhodium-catalyzed [3+2] annulation with alkynes leading to substituted indenones.1 |
| Melting point | 240 °C (dec.)(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) | 26-36/37/39 |
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-Cyanophenylboronic acid primarily used for?
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2-Cyanophenylboronic acid is primarily used as an intermediate in organic synthesis, notably in rhodium-catalyzed annulation reactions with alkynes to produce substituted indenones.
What is the CAS number and molecular formula for 2-Cyanophenylboronic acid?
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The CAS number for 2-Cyanophenylboronic acid is 138642-62-3, and its molecular formula is NCC<sub>6</sub>H<sub>4</sub>B(OH)<sub>2</sub>.
What grade and purity does Tech Serve Solutions supply for 2-Cyanophenylboronic acid?
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Tech Serve Solutions supplies 2-Cyanophenylboronic acid with a minimum assay of 95.0%. We do not represent this product as meeting USP, BP, EP, or pharmacopoeia standards unless explicitly stated in the product documentation.
How should 2-Cyanophenylboronic acid be handled safely?
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2-Cyanophenylboronic acid is a Warning substance (GHS07) that may cause skin irritation (H315), eye irritation (H319), and respiratory irritation (H335). When handling, use a dust mask type N95 (US), wear eyeshields and gloves, and ensure adequate ventilation. Avoid breathing dust and seek fresh air if inhaled. In case of eye contact, rinse cautiously with water for several minutes and seek medical advice.
Is 2-Cyanophenylboronic acid available for export?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals, including 2-Cyanophenylboronic acid, and can fulfil international orders.
How can I request a sample or quote for 2-Cyanophenylboronic acid?
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To request a sample or a quotation for 2-Cyanophenylboronic acid, please contact our sales department through the website or via direct inquiry, providing your specific requirements.
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