Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate

Name: Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate
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CAS No. 736989-93-8
Cat. No. CS-0096050
Purity≥97%
MDL No.MFCD18783177

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Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate|CS-0096050

Structure of 736989-93-8

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General Information

CAS No. 736989-93-8
Cat. No. CS-0096050
Purity ≥97%
MDL No. MFCD18783177
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₁BO₄
Molecular Weight 312.17
Synonym(s) methyl 6-(pinacolboryl)-2-naphthoate
SMILES O=C(C1=CC=C2C=C(B3OC(C)(C)C(C)(C)O3)C=CC2=C1)OC

Description

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate features a boronate ester group appended to a naphthyl scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent integrates seamlessly into complex molecule assembly, offering reliable cross-coupling performance with diverse aryl halides.

Application

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. The naphthyl core provides a rigid, planar scaffold with defined electronic properties, while the tetramethylborolane group ensures high stability, low toxicity, and excellent functional group tolerance. This reagent facilitates efficient C–C bond formation under mild conditions, enabling rapid access to substituted naphthyl architectures relevant in pharmaceutical and materials synthesis. Its bench-stable nature simplifies handling and purification in routine synthetic workflows.

Synthesis

Route1
- 33626-98-1
- In-stock
  
  73183-34-3
- ~93%
- In-stock
  
  736989-93-8
References
- He, Yabing; Zhang, Zhangjing; Xiang, Shengchang; Fronczek, Frank R.; Krishna, Rajamani; Chen, Banglin Chemical Communications, 2012 , vol. 48, # 52 p. 6493 - 6495

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 44.76
LogP 2.9256
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Key Words

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Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate

CAS No. 736989-93-8

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