400727-57-3

Basic information

• Product Name: 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: N,N-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZAMIDE;N,N-DIMETHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZAMIDE;4-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER;3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER;N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-;4-(Dimethylcarbamoyl)benzeneboronic acid, pinacol ester;N-DiMethyl-3-(4;N,N-diMethyl-4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzaMide
• CAS NO: 400727-57-3
• Molecular Formula: C₁₅H₂₂BNO₃
• Molecular Weight: 275.15
• Product Categories: Heterocyclic Compounds
• Mol File: 400727-57-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 406.2 °C at 760 mmHg
• Flash Point: 199.5 °C
• Appearance: /
• Density: 1.06 g/cm³
• Vapor Pressure: 8.28E-07mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.28±0.70(Predicted)
• CAS DataBase Reference: 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER(400727-57-3)
• EPA Substance Registry System: 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER(400727-57-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 400727-57-3(Hazardous Substances Data)

Usage

General Description

3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER is an organoboron compound that is commonly used in organic synthesis. It has a boronic acid functional group, which has been shown to be useful in a variety of reactions, such as Suzuki-Miyaura cross-coupling reactions, which are important in the synthesis of biologically active compounds. The pinacol ester moiety in this compound helps to stabilize the boronic acid functionality and increases its reactivity in various reactions. This chemical is often used as a reagent in the formation of carbon-carbon bonds, making it a valuable tool in the field of organic chemistry.

InChI:InChI=1/C15H22BNO3/c1-14(2)15(3,4)20-16(19-14)12-9-7-11(8-10-12)13(18)17(5)6/h7-10H,1-6H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 405520-68-5 4-(N,N-dimethylaminocarbonyl)phenylboronic acid 
• 18469-37-9 4-bromo-N,N-dimethylbenzamide 
• 73183-34-3 bis(pinacol)diborane 
• 611-74-5 N,N-dimethylbenzamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 180516-87-4 4-carboxyphenylboronic acid pinacol ester 
• 586-75-4 4-chlorobenzoyl chloride 
• 124-40-3 dimethyl amine 
• 586-76-5 4-Bromobenzoic acid 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 24167-56-4 N,N-dimethyl-4-fluorobenzamide 
• 1314987-53-5 4-(6-aminopyridin-3-yl)-N,N-dimethylbenzamide 

Relevant articles and documents

Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles

We herein report the hydrogenation of substituted aryl- and heteroaryl boronate esters for the selective synthesis of cis-substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene-ligated rhodium complex with two dimethyl groups at the ortho-alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom-economic, as well as chemo- and stereoselective route for the generation of cis-configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare.

AMINOPYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS

The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula: (I) where A, B, R1, X1, X2, and W are described herein.

para-Selective C?H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis

para-Selective C?H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C?H borylation and bulky aluminum-based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C?H borylation to give variously substituted (hetero)arylboronates, which are versatile synthetic intermediates for complex multi-substituted aromatic compounds.