2,2'-Bibenzo[d][1,3,2]dioxaborole

Name: 2,2'-Bibenzo[d][1,3,2]dioxaborole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 13826-27-2
Cat. No. CS-W019123
Molecule weightNone
Purity≥98%
MDL No.MFCD09842343

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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2,2'-Bibenzo[d][1,3,2]dioxaborole|CS-W019123

Structure of 13826-27-2

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General Information

CAS No. 13826-27-2
Cat. No. CS-W019123
Purity ≥98%
MDL No. MFCD09842343
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₈B₂O₄
Molecular Weight None
Synonym(s) Bis(catecholato)diboron
SMILES B1(B2OC3=CC=CC=C3O2)OC4=CC=CC=C4O1

Description

2,2'-Bibenzo[d][1,3,2]dioxaborole delivers a stable, electron-rich boronate moiety that integrates seamlessly into cross-coupling reactions. This rigid, planar structure enhances reactivity and resistance to protodeboronation, enabling efficient C–C bond formation under mild conditions. Its bench-stable nature simplifies handling in synthetic workflows.

Application

2,2'-Bibenzo[d][1,3,2]dioxaborole serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its fused dibenzodioxaborole core enhances thermal stability and resistance to protodeboronation, enabling reliable coupling with aryl and heteroaryl halides under mild conditions. The molecule exhibits excellent functional group tolerance and facilitates efficient purification due to its low polarity and high crystallinity, making it ideal for iterative synthesis of complex pharmaceutical scaffolds and conjugated materials.

Synthesis

Route1
- In-stock
  
  1630-79-1
- 120-80-9
- ~74%
- In-stock
  
  13826-27-2
References
- Lawlor, Fiona J.; Norman, Nicholas C.; Pickett, Nigel L.; Robins, Edward G.; Nguyen, Paul; Lesley, Gerry; Marder, Todd B.; Ashmore, Jennifer A.; Green, Jennifer C. Inorganic Chemistry, 1998 , vol. 37, # 20 p. 5282 - 5288
Route2
- In-stock
  
  55718-76-8
- ~41%
- In-stock
  
  13826-27-2
References
- Anastasi, Natia R.; Waltz, Karen M.; Weerakoon, Wimali L.; Hartwig, John F. Organometallics, 2003 , vol. 22, # 2 p. 365 - 369
Route3
- 10294-33-4
- 120-80-9
- ~36%
- In-stock
  
  13826-27-2
References
- Anastasi, Natia R.; Waltz, Karen M.; Weerakoon, Wimali L.; Hartwig, John F. Organometallics, 2003 , vol. 22, # 2 p. 365 - 369

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 36.92
LogP 1.984
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Chemical Synthesis Organometallic Reagents Organoboron Borylation Reagents

Chemical Synthesis Synthetic Reagents C-X(Non-Halogen) Bond Formation Boration

Key Words

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2,2'-Bibenzo[d][1,3,2]dioxaborole

CAS No. 13826-27-2

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