Abstract

[40138-16-7] C7H7BO3 (MW 149.94) InChI = 1S/C7H7BO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5,10-11H InChIKey = DGUWACLYDSWXRZ-UHFFFAOYSA-N (a reagent and substrate that participates in palladium-catalyzed coupling reactions2-9 as well as other metal-catalyzed reactions,10-14 is commonly employed in reductive amination reactions15-18 and certain three-component reactions,19, 20 and as a precursor for other boron derivatives21-24) Physical Data: mp 115–120 °C (contains varying amounts of the anhydride). Solubility: soluble in water (sparingly) and in most of the organic solvents. Form Supplied in: white crystalline solid. Analysis of Reagent Purity: HPLC, IR, NMR. Preparative Methods: refluxing 2-bromobenzaldehyde, ethylene glycol and p-toluenesulfonic acid in toluene for 6 h provides the protected aldehyde. Addition of the aryl bromide to Mg in THF, followed by transfer of the resulting Grignard reagent to a solution of trimethyl borate in THF (−78 °C to room temperature), and subsequent hydrolysis provides the product.25 2-Formylphenylboronic acid can also be prepared by reaction of o-tolylboronic acid with N-bromosuccinimide followed by reaction at reflux with benzoyl peroxide for 6 h.26 Purification: recrystallization from water26 or CH2Cl2/hexane.27 Handling, Storage, and Precautions: the compound should be handled with protective gloves and eyewear in a ventilated area. The compound is stable, but care should be taken to avoid contact with strong oxidizing agents. Hazardous decomposition products include carbon monoxide, carbon dioxide, and boron oxides.

Full Text
Published version (Free)

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call