832114-07-5

Basic information

• Product Name: 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: N,N-DIMETHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZAMIDE;3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER;3-(Dimethylcarbamoyl)benzeneboronic acid, pinacol ester;N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide, 2-[3-(Dimethylcarbamoyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 832114-07-5
• Molecular Formula: C₁₅H₂₂BNO₃
• Molecular Weight: 275.15
• Product Categories: blocks;BoronicAcids;Carboxes
• Mol File: 832114-07-5.mol

Chemical Properties

• Boiling Point: 416.1°C at 760 mmHg
• Flash Point: 205.4°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 3.93E-07mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: Keep Cold
• 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(832114-07-5)
• EPA Substance Registry System: 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER(832114-07-5)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 832114-07-5(Hazardous Substances Data)

Usage

Uses

3-(N,N-Dimethylaminocarbonyl)phenylboronic acid pinacol ester

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

Upstream product

• 611-74-5 N,N-dimethylbenzamide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 24167-51-9 3-bromo-N,N-dimethylbenzamide 
• 73183-34-3 bis(pinacol)diborane 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 1711-09-7 3-bromobenzoyl chloride 

Downstream Products

• 1446086-46-9 cyclohexylcarbamic acid 6-benzyloxy-3′-dimethylcarbamoylbiphenyl-3-yl ester 

Relevant articles and documents

Rational Design and Synthesis of Selective PRMT4 Inhibitors: A New Chemotype for Development of Cancer Therapeutics**

Protein arginine N-methyl transferase 4 (PRMT4) asymmetrically dimethylates the arginine residues of histone H3 and nonhistone proteins. The overexpression of PRMT4 in several cancers has stimulated interest in the discovery of inhibitors as biological tools and, potentially, therapeutics. Although several PRMT4 inhibitors have been reported, most display poor selectivity against other members of the PRMT family of methyl transferases. Herein, we report the structure-based design of a new class of alanine-containing 3-arylindoles as potent and selective PRMT4 inhibitors, and describe key structure–activity relationships for this class of compounds.

Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides

Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.

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.

BIPYRIDYL COMPOUND

There are provided a compound capable of being a novel ligand allowing regioselective borylation to be performed in the aromatic borylation reaction, and a catalyst using the same compound. There is provided a bipyridyl compound represented by a general f

A meta-selective C-H borylation directed by a secondary interaction between ligand and substrate

Regioselective C-H bond transformations are potentially the most efficient method for the synthesis of organic molecules. However, the presence of many C-H bonds in organic molecules and the high activation barrier for these reactions make these transformations difficult. Directing groups in the reaction substrate are often used to control regioselectivity, which has been especially successful for the ortho-selective functionalization of aromatic substrates. Here, we describe an iridium-catalysed meta-selective C-H borylation of aromatic compounds using a newly designed catalytic system. The bipyridine-derived ligand that binds iridium contains a pendant urea moiety. A secondary interaction between this urea and a hydrogen-bond acceptor in the substrate places the iridium in close proximity to the meta-C-H bond and thus controls the regioselectivity. 1 H NMR studies and control experiments support the participation of hydrogen bonds in inducing regioselectivity. Reversible direction of the catalyst through hydrogen bonds is a versatile concept for regioselective C-H transformations.

Synthesis and antitumor activities evaluation of m-(4-morpholinoquinazolin-2-yl)benzamides in vitro and in vivo

In the present study, a series of m-(4-morpholinoquinazolin-2-yl)benzamides were designed, synthesized and characterized. The antiproliferative activities of the synthesized compounds were evaluated against two human cell lines (HCT-116 and MCF-7). Compounds with IC50 values below 4 μM were further evaluated against U-87 MG and A549 cell lines. Among these evaluated compounds, compound T10 displayed a remarkable antiproliferative effect in vitro. The hoechst staining assay showed that compound T10 caused morphological changes. The cell cycle and apoptosis assay further indicated that compound T10 can arrest HCT-116 cells in G2/M and G0/G1 phase and induce apoptosis. PI3K enzyme assays indicated that compounds T7 and T10 selectively inhibit PI3K±. A Western bolt assay further suggested that compound T10 can block the PI3K/Akt/mTOR pathway. Moreover, compound T10 inhibited tumor growth on a mice S180 homograft model. These findings directly identify m-(4-morpholinoquinazolin-2-yl)benzamide derivatives as novel anticancer agents.

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectivel