Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

Name: Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
Brand: ChemScene
Availability: InStock
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CAS No. 454185-98-9
Cat. No. CS-D0735
Purity≥97%
MDL No.MFCD09997797

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Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate|CS-D0735

Structure of 454185-98-9

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General Information

CAS No. 454185-98-9
Cat. No. CS-D0735
Purity ≥97%
MDL No. MFCD09997797
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₁BO₄
Molecular Weight None
Synonym(s) methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate
SMILES O=C(OC)CC1=CC=C(C=C1)B(OC(C)2C)OC2(C)C

Description

Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and resistance to protodeboronation. This bench-stable reagent integrates efficiently into complex molecule synthesis, particularly in late-stage functionalization workflows.

Application

Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions, offering excellent functional group tolerance and bench stability. This reagent facilitates rapid access to biaryl and extended conjugated systems commonly encountered in pharmaceutical and agrochemical synthesis.

Synthesis

Route1
- In-stock
  
  14199-15-6
- ~%
- In-stock
  
  454185-98-9
References
- Wang, You-Chu; Georghiou, Paris E. Organic Letters, 2002 , vol. 4, # 16 p. 2675 - 2678
Route2
- In-stock
  
  41841-16-1
- In-stock
  
  73183-34-3
- ~99%
- In-stock
  
  454185-98-9
References
- SANKYO COMPANY, LIMITED Patent: WO2006/109633 A1, 2006 ; Location in patent: Page/Page column 155-156 ;
Route3
- 147283-85-0
- In-stock
  
  73183-34-3
- ~85%
- In-stock
  
  454185-98-9
References
- Wang, You-Chu; Georghiou, Paris E. Organic Letters, 2002 , vol. 4, # 16 p. 2675 - 2678

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 : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 44.76
LogP 1.7013
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

CAS No. 454185-98-9

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