870195-94-1

Basic information

• Product Name: 2-CHLOROPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: AKOS BRN-1130;2-CHLOROPHENYLBORONIC ACID, PINACOL ESTER;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 2-chlorophenylboronate;2-(2-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Chlorobenzeneboronic acid, pinacol ester
• CAS NO: 870195-94-1
• Molecular Formula: C₁₂H₁₆BClO₂
• Molecular Weight: 238.52
• Product Categories: Heterocyclic Compounds
• Mol File: 870195-94-1.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 140-145 0,05mm
• Flash Point: 144.276°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-CHLOROPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROPHENYLBORONIC ACID, PINACOL ESTER(870195-94-1)
• EPA Substance Registry System: 2-CHLOROPHENYLBORONIC ACID, PINACOL ESTER(870195-94-1)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22
• Safety Statements: 16-36
• RIDADR: 1993
• WGK Germany: 3
• Hazardous Substances Data: 870195-94-1(Hazardous Substances Data)

Usage

General Description

The chemical 2-Chlorophenylboronic acid, pinacol ester is an organoboron compound used in organic synthesis. It consists of a boronic acid group and a chlorophenyl group. It is often used as a reagent in palladium-catalyzed cross-coupling reactions to form carbon-carbon bonds. 2-CHLOROPHENYLBORONIC ACID, PINACOL ESTER is a white solid with a molecular formula of C12H15BClO2 and a molecular weight of 236.51 g/mol. It is important in the field of medicinal and agricultural chemistry for the development of new drugs and agrochemicals.

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

Upstream product

• 95-50-1 1,2-dichloro-benzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-90-7 chlorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 694-80-4 2-bromo-1-chlorobenzene 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 6104-93-4 2-(2-chloro-phenyl)-benzo[1,3,2]dioxaborole 
• 95-51-2 o-chloroaniline 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 22092-92-8 diisopropopylaminoborane 
• 615-41-8 2-iodochlorobenzene 
• 777878-92-9 1,3-dioxoisoindolin-2-yl 2-chlorobenzoate 
• 71-43-2 benzene 

Downstream Products

• 3900-89-8 2-Chlorobenzeneboronic acid 
• 1073629-69-2 6-{[6-(2-chlorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester 
• 1341126-06-4 2-[2-(2,2-difluorovinyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1342256-22-7 (F₃B)C₆H₄(CHCF₂)^(1-)*K⁽¹⁺⁾=K[(F₃B)C₆H₄(CHCF₂)] 
• 95-51-2 o-chloroaniline 
• 16537-16-9 2-chloro-benzoic acid tert-butyl ester 
• 217-59-4 triphenylene 
• 95-57-8 2-monochlorophenol 

Relevant articles and documents

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes

Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.

Photocatalyzed borylation using water-soluble quantum dots

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.