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

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

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.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.