(3aR,3′aR,4R,4′R,6R,6′R,7aS,7′aS)-Dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole

Name: (3aR,3′aR,4R,4′R,6R,6′R,7aS,7′aS)-Dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole
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CAS No. 230299-17-9
Cat. No. CS-0145780
Purity≥97%
MDL No.MFCD02683578

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(3aR,3′aR,4R,4′R,6R,6′R,7aS,7′aS)-Dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole|CS-0145780

Structure of 230299-17-9

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General Information

CAS No. 230299-17-9
Cat. No. CS-0145780
Purity ≥97%
MDL No. MFCD02683578
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₃₂B₂O₄
Molecular Weight 358.09
Synonym(s) Bis[(1S,2S,3R,5S)-pinanediolato]diboron
SMILES CC1([C@@]2([C@]3(OB(O[C@]3(C[C@]1(C2)[H])[H])B4O[C@@]5([C@](C)(O4)[C@]6([H])C[C@]([H])(C5)C6(C)C)[H])C)[H])C

Description

This dodecahydroborole derivative features a rigid, electron-rich scaffold with eight methyl substituents that enhance solubility and stability. The paired boronate moieties enable efficient cross-coupling reactions under mild conditions, while the fused bicyclic framework resists decomposition during storage and handling.

Application

This compound serves as a stable, bench-ready boronate building block with high functional group tolerance. Its rigid, hexamethyl-substituted bicyclic structure enhances thermal stability and resistance to protodeboronation, enabling reliable cross-coupling in Suzuki-Miyaura reactions. The 1,3,2-benzodioxaborole core facilitates efficient palladium-catalyzed transformations, making it particularly valuable for constructing complex heterocyclic scaffolds and fragment-based medicinal chemistry libraries.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 36.92
LogP 3.5214
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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(3aR,3′aR,4R,4′R,6R,6′R,7aS,7′aS)-Dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole

CAS No. 230299-17-9

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