2-(3,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(3,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 401797-02-2
Cat. No. CS-0175551
Purity≥97%
MDL No.None

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2-(3,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0175551

Structure of 401797-02-2

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General Information

CAS No. 401797-02-2
Cat. No. CS-0175551
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅BCl₂O₂
Molecular Weight 272.96
Synonym(s) 3,4-Dichlorophenylboronic Acid, Pinacol Ester
SMILES CC1(C(C)(OB(O1)C2=CC(Cl)=C(Cl)C=C2)C)C

Description

This boronate ester features a 3,4-dichlorophenyl moiety flanked by tetramethyl-substituted dioxaborolane, delivering enhanced stability and moisture tolerance. It integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions, enabling efficient construction of biaryl architectures with high functional group compatibility.

Application

2-(3,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl-substituted dioxaborolane core enhances air and moisture stability, enabling reliable coupling with aryl halides and triflates under standard conditions. The 3,4-dichlorophenyl moiety provides a versatile building block for constructing biaryl scaffolds common in pharmaceutical and agrochemical research.

Synthesis

Route1
- 95-76-1
- In-stock
  
  73183-34-3
- ~72%
- In-stock
  
  401797-02-2
References
- Qiu, Di; Jin, Liang; Zheng, Zhitong; Meng, He; Mo, Fanyang; Wang, Xi; Zhang, Yan; Wang, Jianbo Journal of Organic Chemistry, 2013 , vol. 78, # 5 p. 1923 - 1933
Route2
- 95-50-1
- 25015-63-8
- ~82%
- In-stock
  
  401797-02-2
References
- Rentzsch, Christoph F.; Tosh, Evangeline; Herrmann, Wolfgang A.; Kuehn, Fritz E. Green Chemistry, 2009 , vol. 11, # 10 p. 1610 - 1617
Route3
- In-stock
  
  76-09-5
- 22092-92-8
- 405-02-7
- ~69%
- In-stock
  
  401797-02-2
References
- UNIVERSITE DE BORDEAUX 1; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; PUCHEAULT, Mathieu Jonathan Damien; MARCIASINI, Ludovic Daniel Alain; VAULTIER, Michel Patent: WO2014/9169 A1, 2014 ; Location in patent: Page/Page column 53-54; 67-68 ;

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

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 3.2926
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-(3,4-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 401797-02-2

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