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Organic Building Blocks

Boronic Acids & Esters

Aryl, heteroaryl and alkyl boronic acids, pinacol esters and chiral boranes for Suzuki coupling, asymmetric reduction and boron chemistry.
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The Suzuki-Miyaura reaction made boronic acids one of the most purchased building block classes in medicinal chemistry. This sub-category lists aryl, heteroaryl and alkyl boronic acids, their pinacol esters and specialist chiral boron reagents. Examples include (3,5-Dichlorophenyl)boronic acid, (2-Iodo-5-methoxyphenyl)boronic acid, 1-Ethyl-1H-pyrazole-4-boronic acid pinacol ester, 1-Butylboronic acid and (+)-B-Chlorodiisopinocampheylborane (DIP-Chloride) for asymmetric ketone reduction.

Boronic acids can dehydrate to boroxines on storage, which shifts the apparent assay but rarely harms coupling. Pinacol esters are more stable and easier to purify, though slightly less reactive. Heteroaryl boronic acids, especially 2-pyridyl types, are prone to protodeboronation, so their esters or trifluoroborates are often preferred. Ortho-substituted partners such as the iodo-methoxyphenyl acid allow sequential couplings at two sites.

Products ship in sealed bottles, refrigerated where needed. Each lot comes with a COA and SDS. Gram quantities are typical, with kilogram supply possible for common coupling partners.

Boronic Acids & Esters: questions buyers ask

Should I use a boronic acid or its pinacol ester?
Boronic acids are cheaper and react quickly but can be harder to purify and may vary in assay due to boroxine formation. Pinacol esters are stable, chromatographable and better for unstable heteroaryl groups, at a somewhat higher cost. For routine aryl couplings either works, so choose by availability and stability.
What is protodeboronation and how can I avoid it?
Protodeboronation is the loss of the boron group, replaced by hydrogen, which wastes the coupling partner. It is common with electron-poor and 2-heteroaryl boronic acids under basic aqueous conditions. Using esters, MIDA boronates or trifluoroborates, milder bases and faster catalysts reduces the problem.
What is DIP-Chloride used for?
DIP-Chloride is a chiral borane derived from alpha-pinene. It reduces prochiral ketones, especially aryl alkyl ketones, to secondary alcohols with high enantioselectivity. It is moisture sensitive and should be handled under inert gas. The (+) and (−) forms give opposite alcohol configurations.

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