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diboron-from-xtal-1984-3D-balls-web.png) | |
| Names | |
|---|---|
| Preferred IUPAC name Octamethyl-2,2′-bi-1,3,2-dioxaborolane | |
| Identifiers | |
3D model (JSmol) | |
| Abbreviations | B2pin2 |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.111.245 |
| UNII | |
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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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Bis(pinacolato)diboron is acovalent compound containing twoboron atoms and twopinacolato 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 makingpinacol boronic esters fororganic 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 withpinacol in acidic conditions.[1] The B-B bond length is 1.711(6) Å.
Dehydrogenation ofpinacolborane provides an alternative route:[2]
The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using variousorganorhodium ororganoiridium catalysts, it can also be installed onto saturated hydrocarbons:[3]
These reactions proceed viaboryl complexes.Bis(pinacolato)diboron can also be used as reducing agent for example in transition metal catalyzed hydrogenations of alkenes and alkynes.[4]
