473294
Bis(pinacolato)diboron
99%
Synonym(s):
4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane
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About This Item
Empirical Formula (Hill Notation):
C12H24B2O4
CAS Number:
Molecular Weight:
253.94
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Assay:
99%
Form:
powder (or crystals)
assay
99%
form
powder (or crystals)
mp
137-140 °C (lit.)
SMILES string
CC1(C)OB(OC1(C)C)B2OC(C)(C)C(C)(C)O2
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
InChI key
IPWKHHSGDUIRAH-UHFFFAOYSA-N
General description
Bis(pinacolato)diboron or (B2pin2) 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.
Application
Reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis.
Used to construct a tetramethylpyrrolidine nitroxide scaffold for the synthesis of paramagnetic heterocycles by Suzuki coupling.
Substrate used in a new palladium-catalyzed cyclization of 1,6-enynes leading to homoallylic alkylboronates.
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Articles
Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| 473294-5G | 04061832360843 |
| 473294-100G | 04061832360836 |
| 473294-500MG | 04061833258767 |
| 473294-1G | 04061826672242 |
| 473294-500G | 04061833547793 |
| 473294-25G | 04061835555192 |