179117-44-3

Basic information

• Product Name: 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZAMIDE;4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzaMide
• CAS NO: 179117-44-3
• Molecular Formula: C₁₃H₁₈BNO₃
• Molecular Weight: 247.1
• Product Categories: blocks;BoronicAcids;Carboxes;Heterocyclic Compounds
• Mol File: 179117-44-3.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 388.2 °C at 760 mmHg
• Flash Point: 188.6 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 3.12E-06mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER(179117-44-3)
• EPA Substance Registry System: 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER(179117-44-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 179117-44-3(Hazardous Substances Data)

Usage

General Description

4-Aminocarbonylphenylboronic acid, pinacol ester is a chemical compound that belongs to the class of boronic acids. It is used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER is known for its ability to react with a variety of functional groups, making it a versatile tool in the production of complex organic molecules. Its unique structure and reactive properties make it a valuable component in the development of new pharmaceuticals and agrochemicals, as well as in the study of chemical reactions and mechanisms. Additionally, 4-Aminocarbonylphenylboronic acid, pinacol ester has shown potential as a fluorescent probe for the detection of certain biomolecules.

InChI:InChI=1/C13H18BNO3/c1-12(2)13(3,4)18-14(17-12)10-7-5-9(6-8-10)11(15)16/h5-8H,1-4H3,(H2,15,16)

Upstream product

• 3956-07-8 4-iodobenzamide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 586-76-5 4-Bromobenzoic acid 
• 73183-34-3 bis(pinacol)diborane 
• 180516-87-4 4-carboxyphenylboronic acid pinacol ester 
• 619-56-7 4-chlorobenzamide 
• 698-67-9 p-bromobenzamide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 55-21-0 benzamide 
• 128376-64-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 

Downstream Products

• 951004-38-9 4-[5-(4-carbamoyl-phenyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester 
• 474694-35-4 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}benzamide 
• 1227911-00-3 4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]benzamide 
• 1222999-17-8 C₃₅H₂₁F₃N₄O₂ 
• 1346815-72-2 5-(5-amino-6-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}pyrazin-2-yl)pyridine-2-carboxamide 
• 1401461-76-4 4-{7-[3-((S)-2-Methyl-pyrrolidin-1-yl)-phenylamino]-thiazolo[5,4-d]pyrimidin-5-yl}-benzamide 
• 1415694-84-6 4-(8-(5,6-dimethoxypyridin-2-ylamino)-[1,2,4]-triazolo[1,5-a]pyridin-6-yl)benzamide 2,2,2-trifluoroacetate 
• 1415694-86-8 (S)-4-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide 2,2,2-trifluoroacetate 
• 1419221-53-6 N-(4-(3-fluorooxetan-3-yl)pyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 
• 1419221-56-9 N-(4-(difluoromethyl)pyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 
• 1419223-36-1 N-(4-ethoxypyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 
• 1216771-56-0 4-(2-amino-5-bromopyridin-3-yl)benzamide 

Relevant articles and documents

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2

Dysregulation of translation initiation factor 4E (eIF4E) activity occurs in various cancers. Mitogen-activated protein kinase (MAPK) interacting kinases 1 and 2 (MNK1 and MNK2) play a fundamental role in activation of eIF4E. Structure-activity relationship-driven expansion of a fragment hit led to discovery of dual MNK1 and MNK2 inhibitors based on a novel pyridine-benzamide scaffold. The compounds possess promising in vitro and in vivo pharmacokinetic profiles and show potent on target inhibition of eIF4E phosphorylation in cells.

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.