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

Name: (3aS,3′aS,4S,4′S,6S,6′S,7aR,7′aR)-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. 230299-05-5
Cat. No. CS-0133037
Molecule weight358.09
Purity≥97%
MDL No.MFCD27664803

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(3aS,3′aS,4S,4′S,6S,6′S,7aR,7′aR)-Dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole|CS-0133037

Structure of 230299-05-5

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General Information

CAS No. 230299-05-5
Cat. No. CS-0133037
Purity ≥97%
MDL No. MFCD27664803
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₃₂B₂O₄
Molecular Weight 358.09
Synonym(s) Bis[(+)-pinanediolato]diboron
SMILES C[C@]12[C@@H]3C(C)([C@H](C[C@@]1([H])OB(B4O[C@@]5([C@](C[C@H]6C(C)([C@@H]5C6)C)([H])O4)C)O2)C3)C

Description

This dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole features a sterically shielded boronate core with exceptional bench stability and moisture tolerance. Its rigid, fused bicyclic framework enhances reactivity in Suzuki-Miyaura couplings while minimizing protodeboronation. The eight methyl groups provide steric protection around the boron atom, enabling reliable coupling under standard conditions without requiring inert atmosphere handling.

Application

(3aS,3′aS,4S,4′S,6S,6′S,7aR,7′aR)-Dodecahydro-3a,3′a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its rigid, bicyclic framework enhances thermal stability and resistance to protodeboronation, while the tetrahydronaphthalene-like core provides excellent functional group tolerance. The molecule facilitates efficient C–C bond formation under mild conditions, enabling reliable access to complex molecular architectures in medicinal chemistry and materials synthesis workflows.

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 Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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

CAS No. 230299-05-5

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