Description

Pinacolborane (CAS 25015-63-8) is a highly versatile and reactive organoboron compound with the molecular formula C₆H₁₂BO₂. This colorless to pale yellow liquid is widely recognized for its role as a key reagent in Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in organic synthesis. Its stable dioxaborolane structure, featuring a boron atom coordinated within a pinacol framework, ensures excellent handling and storage stability under inert conditions. Pinacolborane is particularly valued for its ability to transfer boron groups to organic substrates, making it indispensable in pharmaceutical, agrochemical, and materials science research. Supplied in high purity (typically ≥95%), it is packaged under inert gas to maintain reactivity and shelf life. Suitable for use in anhydrous environments, this reagent is a must-have for synthetic chemists and researchers working on advanced boron chemistry applications.

Properties

• CAS Number: 25015-63-8
• Complexity: 106
• InChI: InChI=1S/C6H12BO2/c1-5(2)6(3,4)9-7-8-5/h1-4H3
• InChI Key: LZPWAYBEOJRFAX-UHFFFAOYSA-N
• Exact Mass: 127.0930348
• Molecular Formula: C6H12BO2
• Molecular Weight: 126.97
• SMILES: [B]1OC(C(O1)(C)C)(C)C
• Topological: 18.5
• Monoisotopic Mass: 127.0930348
• Synonyms: Pinacolborane, 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-, EC 607-485-3, DTXSID30422852, DTXCID10373691, 607-485-3, 25015-63-8, Pinacol Borane, boronic acid pinacol ester, MFCD00674030, Pinacolboronane, Hbpin, Pinacolatoborane, BA5Z9NE6HM, SCHEMBL80492, SCHEMBL125339, Pinacolborane, 1.0M in THF, UCFSYHMCKWNKAH-UHFFFAOYSA-N, BCP24406, AC-783, SBB062776, AKOS005137948, CS-W016554, AC-37631, AS-40957, 4,4,5,5-tetramethyl-1,3,2^{2}, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan, 4,4,5,5 tetramethyl-1,3,2 dioxaborolane, 4,4,5,5-tetramethyl-[1,3,2]dioxaborolan, NS00002433, T2572, 4,4,5,5-Tetramethyl-[1,3,2]dioxaborolane, EN300-73933, 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane, 4,4,5,5,-tetramethyl-[1,3,2]-dioxaborolane, 4,4,5,5-tetramethyl-1,3,2lambda2-dioxaborolane, A817600, 4,4,5,5-tetramethyl-1,3,2^{2}-dioxaborolane, 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane, 97%, 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane; Pinacolatoborane;

Application

Pinacolborane is extensively used in organic synthesis as a boron source for Suzuki-Miyaura cross-coupling reactions, facilitating the construction of biaryl compounds. It serves as a critical reagent in the preparation of boronic esters and acids, which are intermediates in drug discovery and material science. Additionally, its applications extend to catalytic borylation reactions and polymer chemistry, where it modifies molecular structures to achieve desired properties.

Safety and Hazards

GHS Hazard Statements

• H220 (18%): Extremely flammable gas [Danger Flammable gases]
• H225 (99.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]
• H260 (56.6%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]
• H261 (24.9%): In contact with water releases flammable gas [Danger Substances and mixtures which in contact with water, emit flammable gases]
• H315 (57.1%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (69.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P203, P210, P222, P223, P231+P232, P233, P240, P241, P242, P243, P264, P264+P265, P280, P302+P335+P334, P302+P352, P303+P361+P353, P305+P354+P338, P317, P321, P332+P317, P362+P364, P370+P378, P377, P381, P402+P404, P403, P403+P235, and P501

Hazard Classes and Categories

• Flam. Gas 1 (18%)
• Flam. Liq. 2 (99.5%)
• Water-react. 1 (56.6%)
• Water-react. 2 (24.9%)
• Skin Irrit. 2 (57.1%)
• Eye Dam. 1 (69.8%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.