1212021-11-8

Basic information

• Product Name: 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• Synonyms: 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;3-Chloro-5-cyanophenylboronic acid, pinacol ester;3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
• CAS NO: 1212021-11-8
• Molecular Formula: C₁₃H₁₅BClNO₂
• Molecular Weight: 263.5277
• Mol File: 1212021-11-8.mol

Chemical Properties

• Boiling Point: 361.1±32.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerated.
• CAS DataBase Reference: 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile(1212021-11-8)
• EPA Substance Registry System: 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile(1212021-11-8)

Safety Data

• Hazardous Substances Data: 1212021-11-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is used as a synthetic reagent for the creation of carbon-carbon bonds in the development of new pharmaceutical compounds. Its role in palladium-catalyzed cross-coupling reactions is crucial for the synthesis of complex organic molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is employed as a key reagent in the synthesis of agrochemicals. Its involvement in cross-coupling reactions allows for the production of novel compounds with pesticidal or herbicidal properties, contributing to the development of more effective and targeted crop protection agents.
Used in Materials Science:
3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is utilized as a synthetic building block in the preparation of functionalized materials. Its application in cross-coupling reactions enables the synthesis of materials with tailored properties, such as improved conductivity, stability, or specific binding affinities, which can be applied in various high-tech industries.

Upstream product

• 766-84-7 3-chloro-benzonitrile 
• 73183-34-3 bis(pinacol)diborane 
• 289039-30-1 3-chloro-5-iodobenzonitrile 

Downstream Products

• 1383983-62-7 3-(4-amino-5-methyl-3'H-dispiro[cyclopropane-1,2'-indene-1',2-imidazol]-6'-yl)-5-chlorobenzonitrile 
• 1442416-13-8 C₁₆H₁₄ClN 
• 34662-30-1 1-nitro-3-chloro-5-cyanobenzene 
• 1245509-42-5 C₂₈H₂₅ClN₄O 

Relevant articles and documents

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

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