68716-51-8

Basic information

• Product Name: 3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 2-(3,5-DICHLOROPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER;5-Dichlorophenyl)-4;1,3,2-Dioxaborolane,2-(3,5-dichlorophenyl)-4,4,5,5-tetraMethyl-;3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER, 95+%;1,3-Dichloro-5-(pinacolboryl)benzene;3,5-Dichlorobenzeneboronic acid pinacol ester;2-(3,5-Dichlorophenyl)
• CAS NO: 68716-51-8
• Molecular Formula: C₁₂H₁₅BCl₂O₂
• Molecular Weight: 272.96
• Product Categories: Heterocyclic Compounds
• Mol File: 68716-51-8.mol
• Article Data: 43

Chemical Properties

• Melting Point: 51.0 to 55.0 °C
• Boiling Point: 351.1 °C at 760 mmHg
• Flash Point: 166.1 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 8.51E-05mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER(68716-51-8)
• EPA Substance Registry System: 3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER(68716-51-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 68716-51-8(Hazardous Substances Data)

Usage

General Description

3,5-Dichlorophenylboronic acid, pinacol ester is a chemical compound that belongs to the class of boronic esters. It is commonly used as a building block in organic synthesis for the production of pharmaceuticals, agrochemicals, and other specialty chemicals. 3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER is known for its ability to react with various reagents to form carbon-carbon and carbon-heteroatom bonds, making it a valuable tool in the field of organic chemistry. Additionally, it has been used in the development of new methods for cross-coupling reactions and functional group transformations, making it a versatile and important compound in the field of synthetic chemistry.

InChI:InChI=1/C12H15BCl2O2/c1-11(2)12(3,4)17-13(16-11)8-5-9(14)7-10(15)6-8/h5-7H,1-4H3

Upstream product

• 541-73-1 1,3-Dichlorobenzene 
• 626-43-7 3,5-Dichloroaniline 
• 73183-34-3 bis(pinacol)diborane 
• 3032-81-3 3,5-dichloroiodobenzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 19752-55-7 1-bromo-3,5-dichlorobenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 22092-92-8 diisopropopylaminoborane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 67492-50-6 (3,5-dichlorophenyl)boronic acid 

Downstream Products

• 591-35-5 3,5-dichlorophenol 
• 626-43-7 3,5-Dichloroaniline 
• 618-62-2 3,5-dichloro-1-nitrobenzene 
• 864725-22-4 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene 
• 943137-86-8 3-(5-chloro-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole 
• 950482-85-6 5-(3,5-dichlorophenyl)-3-(5,6-dichloro-3-pyridyl)-5-trifluoromethyl-4,5-dihydroisoxazole 
• 1070396-58-5 C₁₇H₁₁Cl₂F₄NO₂ 
• 1007317-81-8 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-fluorobenzonitrile 
• 930110-39-7 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoronitrobenzene 
• 1125812-44-3 3-(3-bromo-4-fluorophenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole 
• 1413285-46-7 5-(3,5-dichlorophenyl)-3-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole 
• 864736-38-9 C₁₇H₈Cl₂F₇NO 
• 920502-13-2 C₁₆H₉Cl₂F₄NO 

Relevant articles and documents

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation

Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C-H borylation/N-C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C-H borylation and divergent acyl and decarbonylative amide N-C(O) and C-C activation. The methodology diverts the traditional acylation and arylation regioselectivity, allowing us to directly utilize readily available arenes and amides to produce valuable ketone and biaryl motifs.

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.