4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane
Brand: ChemScene
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CAS No. 68716-52-9
Cat. No. CS-0153835
Purity≥98%
MDL No.MFCD05663869

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4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane|CS-0153835

Structure of 68716-52-9

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General Information

CAS No. 68716-52-9
Cat. No. CS-0153835
Purity ≥98%
MDL No. MFCD05663869
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₉BO₂
Molecular Weight 254.13
Synonym(s) Naphthalene-1-boronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=CC=CC3=CC=CC=C32)O1

Description

This boronate ester integrates a naphthalen-1-yl group with a sterically shielded tetramethylcyclopentadienone core, enabling stable coupling in Suzuki-Miyaura reactions. The electron-rich aryl moiety enhances reactivity under standard conditions, while the hindered substituents confer robustness to hydrolysis and air exposure.

Application

4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its naphthyl moiety enables efficient incorporation into extended π-systems and heterocyclic scaffolds. The tetramethyl-substituted dioxaborolane offers enhanced stability and mild reaction conditions, facilitating functional group tolerance and straightforward purification—ideal for iterative synthesis in medicinal chemistry and materials science workflows.

Synthesis

Route1
- In-stock
  
  90-11-9
- In-stock
  
  73183-34-3
- ~68%
- In-stock
  
  68716-52-9
References
- Green Chemistry, , vol. 14, # 3 p. 661 - 667
Route2
- 61676-62-8
- In-stock
  
  90-11-9
- ~93%
- In-stock
  
  68716-52-9
References
- Organic Letters, , vol. 13, # 13 p. 3312 - 3315
Route3
- In-stock
  
  90-14-2
- In-stock
  
  73183-34-3
- ~94%
- In-stock
  
  68716-52-9
References
- Journal of the American Chemical Society, , vol. 135, # 50 p. 18730 - 18733

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-H335
Precautionary Statements : P233-P260-P261-P264-P271-P280-P302+P352-P304+P340-P340-P362-P403-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 3.139
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

68716-52-9 sigma68716-52-9 manufacturer68716-52-9 price68716-52-9 structure68716-52-9 SDSbuy 68716-52-968716-52-9 supplier68716-52-9 uses68716-52-9 molecular weightprice of 68716-52-968716-52-9 chemical name formula of 68716-52-9

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4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane

CAS No. 68716-52-9

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