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Names | |
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Preferred IUPAC name
Octamethyl-2,2′-bi-1,3,2-dioxaborolane | |
Identifiers | |
3D model (
JSmol)
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Abbreviations | B2pin2 |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.111.245 |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C12H24B2O4 | |
Molar mass | 253.94 g·mol−1 |
Melting point | 137 to 140 °C (279 to 284 °F; 410 to 413 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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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. [1]
This compound may be prepared by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions. [1] The B-B bond length is 1.711(6) Å.
Dehydrogenation of pinacolborane provides an alternative route: [2]
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: [3]
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. [4]