6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol

Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol
Brand: ChemScene
Availability: InStock
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CAS No. 269410-21-1
Cat. No. CS-0174969
Purity≥95%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol|CS-0174969

Structure of 269410-21-1

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General Information

CAS No. 269410-21-1
Cat. No. CS-0174969
Purity ≥95%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₉BO₃
Molecular Weight 270.13
Synonym(s) 6-(Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol
SMILES CC1(C(C)(OB(O1)C2=CC=C3C=C(O)C=CC3=C2)C)C

Description

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol features a boronate ester group conjugated to a naphthol scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and resistance to hydrolysis, while the phenolic OH facilitates directional functionalization. This bench-stable reagent integrates readily into complex molecule assembly workflows.

Application

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol serves as a versatile boronate building block for Suzuki-Miyaura coupling, enabling efficient C–C bond formation under mild conditions. Its naphthol functionality offers enhanced stability and facilitates orthogonal functional group handling. The pinacol boronate moiety ensures excellent bench stability, ease of purification, and compatibility with diverse reaction partners, making it ideal for constructing complex heterocyclic scaffolds and advanced API intermediates in medicinal chemistry and materials science workflows.

Synthesis

Route1
- In-stock
  
  15231-91-1
- In-stock
  
  73183-34-3
- ~77%
- In-stock
  
  269410-21-1
References
- LG CHEM, LTD. Patent: WO2009/28902 A2, 2009 ; Location in patent: Page/Page column 54 ;
Route2
- In-stock
  
  15231-91-1
- 25015-63-8
- ~%
- In-stock
  
  269410-21-1
References
- Commonwealth Scientific and Industrial Research Organisation Patent: US6680401 B1, 2004 ; Location in patent: Page column 64 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 38.69
LogP 2.8446
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Key Words

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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol

CAS No. 269410-21-1

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