(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)boronic acid

Name: (2,2-Difluorobenzo[d][1,3]dioxol-5-yl)boronic acid
Brand: ChemScene
Availability: InStock
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CAS No. 190903-71-0
Cat. No. CS-W020428
Purity≥95%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)boronic acid|CS-W020428

Structure of 190903-71-0

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General Information

CAS No. 190903-71-0
Cat. No. CS-W020428
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅BF₂O₄
Molecular Weight 201.92
Synonym(s) 2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid
SMILES FC(O1)(F)OC2=C1C=CC(B(O)O)=C2

Description

This boronate moiety integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, delivering high functional group tolerance and stability under standard conditions. The difluorinated aryl scaffold enhances metabolic resilience and electron-deficient character, enabling efficient coupling with diverse halides and pseudohalides.

Application

(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient access to fluorinated biaryl architectures. Its stability under ambient conditions and compatibility with diverse functional groups facilitate straightforward purification and integration into complex molecular frameworks. The difluorinated aromatic core enhances metabolic stability and modulates electronic properties, making it valuable for medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  33070-32-5
- 5419-55-6
- ~73%
- In-stock
  
  190903-71-0
References
- Dominique, Romyr; Goodnow, JR., Robert Alan; Kowalczyk, Agnieszka; Qiao, Qi; Sidduri, Achyutharao; Tilley, Jefferson Wright Patent: US2010/240678 A1, 2010 ; Location in patent: Page/Page column 66 ;
Route2
- In-stock
  
  33070-32-5
- ~%
- In-stock
  
  190903-71-0
References
- Hasvold, Lisa A.; Wang, Weibo; Gwaltney II, Stephen L.; Rockway, Todd W.; Nelson, Lissa T. J.; Mantei, Robert A.; Fakhoury, Stephen A.; Sullivan, Gerard M.; Li, Qun; Lin, Nan-Horng; Wang, Le; Zhang, Haiying; Cohen, Jerome; Gu, Wen-Zhen; Marsh, Kennan; Bauch, Joy; Rosenberg, Saul; Sham, Hing L. Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 22 p. 4001 - 4005

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 58.92
LogP -0.3121
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Benzodioxolane compounds

Key Words

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(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)boronic acid

CAS No. 190903-71-0

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