863578-36-3

Basic information

• Product Name: 2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER;5-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine
• CAS NO: 863578-36-3
• Molecular Formula: C₁₃H₂₀BNO₂
• Molecular Weight: 233.11
• Mol File: 863578-36-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 68 °C(Solv: hexane (110-54-3))
• Boiling Point: 347.2 °C at 760 mmHg
• Flash Point: 163.8 °C
• Appearance: /
• Density: 1.03 g/cm³
• Vapor Pressure: 5.47E-05mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.02±0.11(Predicted)
• CAS DataBase Reference: 2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER(863578-36-3)
• EPA Substance Registry System: 2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER(863578-36-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 863578-36-3(Hazardous Substances Data)

Usage

Uses

2-Amino-4-methylphenylboronic acid, pinacol ester

InChI:InChI=1/C13H20BNO2/c1-9-6-7-10(11(15)8-9)14-16-12(2,3)13(4,5)17-14/h6-8H,15H2,1-5H3

Upstream product

• 5326-34-1 4-Bromo-3-nitrotoluene 
• 53078-85-6 2-bromo-5-methylaniline 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 113623-79-3 5-methyl-2-(pyridin-2-yl)benzenamine 
• 1579291-57-8 (9H-fluoren-9-yl)methyl 4-(2-azido-4-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 1579291-80-7 2-azido-4-methylphenylboronic acid pinacolate ester 
• 1082470-14-1 methyl 2,6-dimethylindole-3-carboxylate 
• 1352874-51-1 4'-[3-(2-chloro-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-4-methyl-biphenyl-2-ylamine trifluoroacetic acid 

Relevant articles and documents

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines

A Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro α,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon-carbon and carbon-nitrogen bond formation in a single reaction vessel. The requisite β-chloro α,β-unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)2 is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram-scale synthesis of a trispheridine alkaloid.

MK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.