2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
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CAS No. 376584-76-8
Cat. No. CS-0092138
Purity≥97%
MDL No.MFCD08063145

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2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0092138

Structure of 376584-76-8

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General Information

CAS No. 376584-76-8
Cat. No. CS-0092138
Purity ≥97%
MDL No. MFCD08063145
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇BO₂S
Molecular Weight 260.16
Synonym(s) BENZO(B)THIOPHENE-2-BORONIC ACID, PINACOL ESTER
SMILES CC1(C)C(C)(C)OB(C2=CC3=CC=CC=C3S2)O1

Description

This boronate ester integrates a benzo[b]thiophene moiety with a stable, bench-ready dioxaborolane core. It enables efficient Suzuki-Miyaura coupling under standard conditions, delivering fused heterocyclic architectures with high functional group tolerance and minimal byproduct formation.

Application

2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its benzo[b]thiophene moiety enables efficient construction of biaryl scaffolds prevalent in pharmaceutical and agrochemical research. The tetramethyl-substituted dioxaborolane enhances shelf stability and minimizes protodeboronation, while facilitating straightforward purification and compatibility with diverse reaction conditions.

Synthesis

Route1
- 61676-62-8
- In-stock
  
  95-15-8
- ~83%
- In-stock
  
  376584-76-8
References
- Sandee, Albertus J.; Williams, Charlotte K.; Evans, Nicholas R.; Davies, John E.; Boothby, Clare E.; Koehler, Anna; Friend, Richard H.; Holmes, Andrew B. Journal of the American Chemical Society, 2004 , vol. 126, # 22 p. 7041 - 7048
Route2
- In-stock
  
  73183-34-3
- In-stock
  
  95-15-8
- ~83%
- In-stock
  
  376584-76-8
References
- Tagata, Tsuyoshi; Nishida, Mayumi; Nishida, Atsushi Advanced Synthesis and Catalysis, 2010 , vol. 352, # 10 p. 1662 - 1666
Route3
- 25015-63-8
- In-stock
  
  95-15-8
- ~96%
- In-stock
  
  376584-76-8
References
- Ishiyama, Tatsuo; Nobuta, Yusuke; Hartwig, John F.; Miyaura, Norio Chemical Communications, 2003 , # 23 p. 2924 - 2925

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 18.46
LogP 3.2005
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzothiophene compounds

Key Words

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2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 376584-76-8

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