863868-30-8

Basic information

• Product Name: 2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER
• Synonyms: 2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER;4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• CAS NO: 863868-30-8
• Molecular Formula: C13H17BClNO3
• Molecular Weight: 263.53
• Mol File: 863868-30-8.mol

Chemical Properties

• Boiling Point: 364.9±32.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER(863868-30-8)
• EPA Substance Registry System: 2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER(863868-30-8)

Safety Data

• Hazardous Substances Data: 863868-30-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER is used as a building block for the synthesis of various pharmaceutical compounds. It is commonly used in Suzuki coupling reactions to form carbon-carbon bonds, which is crucial in the development of new drug candidates.
Used in Agrochemical Industry:
2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER is also used as a building block in the synthesis of agrochemical compounds. Its application in Suzuki coupling reactions aids in the preparation of complex organic molecules for use in the agrochemical sector.
Used in Organic Synthesis:
2-CHLORO-5-CYANOPHENYL BORONIC ACID PINACOL ESTER is used as a reagent in organic synthesis for the formation of carbon-carbon bonds. This makes it a valuable component in the preparation of complex organic molecules and contributes to the advancement of chemical research and development.

Upstream product

• 948549-53-9 3-bromo-4-chlorobenzonitrile 
• 73183-34-3 bis(pinacol)diborane 
• 623-03-0 4-Cyanochlorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant articles and documents

Zig-Zag Type Molecular Design Strategy of N-Type Hosts for Sky-Blue Thermally-Activated Delayed Fluorescence Organic Light-Emitting Diodes

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C-H Borylation Catalysts that Distinguish between Similarly Sized Substituents like Fluorine and Hydrogen

By modifying ligand steric and electronic profiles it is possible to C-H borylate ortho or meta to substituents in aromatic and heteroaromatic compounds, where steric differences between accessible C-H sites are small. Dramatic effects on selectivities between reactions using B2pin2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) are described for the first time. Judicious ligand and borane combinations give highly regioselective C-H borylations on substrates where typical borylation protocols afford poor selectivities.

Process for producing cyano substituted arene boranes and compounds

A process for producing cyano substituted arene boranes is described. The compounds are useful intermediates to pharmaceutical compounds using the cyano group as a reactant.

Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles

Ir-catalyzed borylations of 4-substituted benzonitriles are described. In contrast to electrophilic aromatic substitutions and directed ortho metalations, C-H activation/borylation enables functionalization at the 2-position, adjacent to the cyano group, when the 4-subsitutent is larger than cyano. When an excess of borane reagent is used, diborylation can be achieved with a single regioisomer being formed in certain cases. Extension of sterically directed borylation to cyano-substituted, five- and six-membered ring heterocycles is also reported.