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Bis(pinacolato)diboron (B2pin2)
Bis(pinacolato)diboron (B2pin2) | CAS 73183-34-3 | ≥98%
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Technical Specifications
| CAS Number | 73183-34-3 |
| EC / EINECS Number | 615-925-0 |
| MDL Number | MFCD00799570 |
| SMILES | B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C |
| InChI | InChI=1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3 |
| InChIKey | IPWKHHSGDUIRAH-UHFFFAOYSA-N |
| PubChem CID | 2733548 |
| Molecular Formula | C₁₂H₂₄B₂O₄ |
| Molecular Weight | 253.9 g/mol |
| Melting Point | 137-140 °C (lit.) |
| Solubility | Soluble in tetrahydrofuran, dichloromethane, toluene, hexane, heptane. Insoluble in: water |
| Purity | ≥98% |
| Physical Form | White crystalline solid |
| HS Code | 2920.90 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Keep refrigerated. Keep container tightly closed. Keep away from heat. |
Product Description & Scientific Applications
Bis(pinacolato)diboron (B₂pin₂) is 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane, two pinacol boronate esters joined by a B–B bond. The white crystalline solid melts at 137–140 °C and dissolves in methanol, ethanol and benzene. Neither boron is nucleophilic on its own: the tetraalkoxydiboron core lacks nucleophilic character and its electrophilicity is suppressed. A Lewis base binds one of the two borons. The adduct renders the second boron nucleophilic, and it hands over the boryl group. That activation makes B₂pin₂ one of the principal reagents for installing boron in an organic molecule.
Miyaura borylation. Palladium adds oxidatively to an aryl halide or triflate, transmetalates the diboron, and reductively eliminates the arylboronate. Potassium acetate is the operative base; it displaces halide to give ArPdOAc, the species that transmetalates. Phosphate and carbonate divert material to homocoupled biaryl.
Iridium C–H borylation. An iridium catalyst with di-tert-butylbipyridine borylates arene and heteroarene C–H bonds directly. The active species is sterically crowded, so the most accessible position reacts; five-membered heteroarenes borylate at C-5.
Copper–boryl addition. Copper with an alkoxide base delivers Bpin to the β-carbon of unsaturated ketones, esters, nitriles and phosphonates. Chiral ligands make the same system enantioselective.
Diboration. Platinum adds both halves across an alkyne to give cis-vicinal diborylalkenes.
Transition-metal-free transfer. Isolated Lewis-base adducts boryl-transfer to aryl halides and diazonium salts with no metal present.
Shipping Destinations
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Safety Information
| Hazard Class | Not regulated for transport |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
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