1,3-Benzodioxole, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Name: 1,3-Benzodioxole, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 94838-82-1
Cat. No. CS-0029530
Purity≥97%
MDL No.MFCD05663889

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1,3-Benzodioxole, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-|CS-0029530

Structure of 94838-82-1

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General Information

CAS No. 94838-82-1
Cat. No. CS-0029530
Purity ≥97%
MDL No. MFCD05663889
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BO₄
Molecular Weight 248.08
Synonym(s) 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole
SMILES CC1(C)C(C)(C)OB(C2=CC=C(OCO3)C3=C2)O1

Description

This boronate ester features a benzo[d][1,3]dioxol-5-yl moiety integrated with a tetramethyl-substituted dioxaborolane ring, delivering enhanced stability and reactivity in cross-coupling processes. The electron-rich aromatic system pairs with the bench-stable boronate functionality, enabling efficient Suzuki-Miyaura coupling under mild conditions.

Application

2-(Benzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its 1,3-dioxaborolane moiety exhibits excellent functional group tolerance and compatibility with diverse aryl and heteroaryl electrophiles. The benzo[d][1,3]dioxol-5-yl group provides a rigid, electron-rich scaffold useful in constructing bioactive heterocycles and pharmaceutical intermediates.

Synthesis

Route1
- In-stock
  
  5876-51-7
- 25015-63-8
- ~73%
- In-stock
  
  94838-82-1
References
- Commonwealth Scientific and Industrial Research Organisation Patent: US6680401 B1, 2004 ; Location in patent: Page column 26 ;
Route2
- In-stock
  
  2635-13-4
- 61676-62-8
- ~99%
- In-stock
  
  94838-82-1
References
- Ebner, David C.; Bagdanoff, Jeffrey T.; Ferreira, Eric M.; McFadden, Ryan M.; Caspi, Daniel D.; Trend, Raissa M.; Stoltz, Brian M. Chemistry - A European Journal, 2009 , vol. 15, # 47 p. 12978 - 12992
Route3
- 16387-85-2
- In-stock
  
  73183-34-3
- ~82%
- In-stock
  
  94838-82-1
References
- Chow, Wing Kin; So, Chau Ming; Lau, Chak Po; Kwong, Fuk Yee Chemistry - A European Journal, 2011 , vol. 17, # 25 p. 6913 - 6917

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 36.92
LogP 1.7145
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzodioxolane compounds

Key Words

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1,3-Benzodioxole, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

CAS No. 94838-82-1

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