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    • Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH3)4C2O2B]2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, B2pin2 is not moisture-sensitive and can be handled in air.


    Preparation and structure


    This compound may be prepared by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions. The B-B bond length is 1.711(6) Å.
    Dehydrogenation of pinacolborane provides an alternative route:

    2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2


    Reactions



    The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons:

    CH3(CH2)6CH3 + [pinB]2 → pinBH + CH3(CH2)7Bpin
    These reactions proceed via boryl complexes.
    Bis(pinacolato)diboron can also be used as reducing agent for example in transition metal catalyzed hydrogenations of alkenes and alkynes.


    References

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Bis(pinacolato)diboron - Wikipedia

Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH 3 ) 4 C 2 O 2 B] 2 ; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B 2 pin 2 .

Bis(pinacolato)diboron 99 73183-34-3 - MilliporeSigma

Bis(pinacolato)diboron or (B 2 pin 2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

Bis(pinacolato)diboron | 73183-34-3 - ChemicalBook

27 Jan 2025 · Bis(pinacolato)diboron or (B 2 pin 2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

Bis(pinacolato)diborane | C12H24B2O4 | CID 2733548 - PubChem

Bis(pinacolato)diboron is a 1,3,2-dioxaborolane that is 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in which the boron hydrogen at position 2 is replaced by a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. It is a reagent used in organic synthesis to synthesise pinacol boronic esters.

Bis(pinacolato)diboron, 98+%, Thermo Scientific Chemicals

Bis(pinacolato)diboron is a reagent used for the cis-vicinal diborylation of acetylenes and olefins with platinum catalysis. It acts as a substrate used in a new palladium-catalyzed cyclization of 1,6-enynes leading to homoallylic alkylboronates.

Bis(pinacolato)diboron - 4,4 - MilliporeSigma

Bis(pinacolato)diboron. Synonyms: 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane. CAS 73183-34-3. Molecular Weight 253.94. Browse …

Bis(pinacolato)diboron: Synthesis and applications - ChemicalBook

25 Feb 2020 · Bis(pinacolato)diboron is an important organic intermediate. In Suzuki reaction, it has the advantages of high reaction selectivity, mild conditions, and high yield.