195062-61-4

Basic information

• Product Name: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CHLOROBENZENE
• Synonyms: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CHLOROBENZENE;4-CHLOROPHENYLBORONIC ACID, PINACOL ESTER;2-(4-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Chlorobenzeneboronic acid, pinacol ester;4-Chlorophenylboronic acid pinacol ester 97%;Pinacol (4-chlorophenyl)boronate
• CAS NO: 195062-61-4
• Molecular Formula: C₁₂H₁₆BClO₂
• Molecular Weight: 238.52
• Product Categories: Aryl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 195062-61-4.mol
• Article Data: 117

Chemical Properties

• Melting Point: 50-55 °C(lit.)
• Boiling Point: 308.678 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: White to pale brown/Solid
• Density: 1.103 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• CAS DataBase Reference: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CHLOROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CHLOROBENZENE(195062-61-4)
• EPA Substance Registry System: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CHLOROBENZENE(195062-61-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 195062-61-4(Hazardous Substances Data)

Usage

Uses

4-Chlorophenylboronic acid pinacol ester can be used as a reagent in Suzuki-Miyaura cross-coupling reaction to form C-C bonds by reacting with different aryl halides over palladium catalysts. It can also be used as a reactant: To prepare 2-(4-chlorophenyl)-4H-chromen-4-one by treating with 4-chromanone via one-pot palladium-catalyzed dehydrogenation and oxidative boron-Heck coupling reaction. In the ligand-enabled C-H bond activation reaction in the presence of a palladium catalyst. To synthesize biaryl amides via Cu-catalyzed C-H bond coupling of aryl arylamides.

InChI:InChI=1/C12H16BClO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,1-4H3

Upstream product

• 106-39-8 bromochlorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 106-46-7 para-dichlorobenzene 
• 106-47-8 4-chloro-aniline 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1321604-74-3 C₁₀H₁₄BClN₂ 
• 1679-18-1 4-Chlorophenylboronic acid 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 52010-59-0 1-(4-chlorophenyl)-3,3-diethyltriaz-1-ene 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 106-37-6 1.4-dibromobenzene 
• 67-72-1 hexachloroethane 
• 108-90-7 chlorobenzene 

Downstream Products

• 106-48-9 4-chloro-phenol 
• 1256781-67-5 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1256781-68-6 2-(3-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1309607-19-9 4,4,5,5-tetramethyl-2-(4-(1-phenylethyl)phenyl)-1,3,2-dioxaborolane 
• 623-03-0 4-Cyanochlorobenzene 
• 91813-37-5 2-(4-chlorophenyl)thiazolo<5,4-b>pyridine 
• 1613415-67-0 (R)-4-(4-chlorophenyl)-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide 
• 1533422-45-5 C₁₂H₁₃ClF₃NO₄S 
• 1612891-24-3 3,4,5-trifluoro-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline 
• 40133-23-1 2-(4-chlorophenyl)thiophene 

Relevant articles and documents

Electrochemical reduction of polyhalogenated aryl derivatives in the presence of pinacolborane: Electrosynthesis of functionalised arylboronic esters

The electroreduction of several dihalogenated aryl compounds was carried out in the presence of pinacolborane as the electrophile for the synthesis of halogenated arylboronic ester derivatives. The nature and the relative position of the halogen substituents strongly influence the boration results. The electroreduction of a trihalogenated derivative was also examined. Reactions were carried out in THF in a single-compartment cell in the presence of a Mg anode.

Palladium-Catalyzed Chemoselective Borylation of (Poly)halogenated Aryl Triflates and Their Application in Consecutive Reactions

This study reports the palladium-catalyzed chemoselective borylation of (poly)halogenated aryl triflates with a reactivity order of C?Cl>C?OTf. A catalyst system comprising Pd(OAc)2 and SelectPhos (L1) enables a reaction with high reactivity and chemoselectivity. The consecutively chemoselective borylation reaction followed by the chemoselective intermolecular Suzuki-Miyaura reaction can be performed using a one-pot two-step approach to synthesize unsymmetrical biaryl compounds containing the triflate moiety. The reaction can be scaled up to the gram scale without diminishing the yield and chemoselectivity. (Figure presented.).

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds