1381957-27-2

Basic information

• Product Name: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate
• CAS NO: 1381957-27-2
• Molecular Weight: 338.211
• Mol File: 1381957-27-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 458.0±38.0 °C(Predicted)
• Density: 1.12±0.1 g/cm3(Predicted)
• CAS DataBase Reference: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate(1381957-27-2)
• EPA Substance Registry System: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate(1381957-27-2)

Safety Data

• Hazardous Substances Data: 1381957-27-2(Hazardous Substances Data)

Usage

General Description

Methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is a chemical compound with the molecular formula C23H27BO4. It is used as a reagent for the Suzuki-Miyaura cross-coupling reaction, which is a widely used method in organic synthesis for the formation of carbon-carbon bonds. methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is a boronic ester, which means it contains a boron atom bonded to an alkyl or aryl group and an ester functional group. Boronic esters are important intermediates in the synthesis of pharmaceuticals, agrochemicals, and materials. Methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate is a valuable building block for the production of complex organic molecules in chemical and pharmaceutical research.

Upstream product

• 619-44-3 methyl 4-iodobenzoate 
• 5467-74-3 4-Bromophenylboronic acid 
• 49742-56-5 methyl 4-(4-tolyl)benzoate 
• 73183-34-3 bis(pinacol)diborane 
• 89901-02-0 methyl 4′-chloro-[1,1′-biphenyl]-4-carboxylate 
• 89901-03-1 methyl 4’-bromo-[1,1’-diphenyl]-4-carboxylate 
• 100-01-6 4-nitro-aniline 
• 171364-83-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 106-50-3 1,4-phenylenediamine 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 

Downstream Products

• 1595145-37-1 4-(4-{6-[(2S)-2-{[2-(4-cyanophenyl)ethyl]carbamoyl}azetidin-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl}phenyl)benzoic acid 
• 1595145-35-9 (S)-methyl 4'-(6-(2-((4-cyanophenylethyl)carbamoyl)azetidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)-[1,1'-biphenyl]-4-carboxylate 

Relevant articles and documents

Two-dimensional crystals from reduced symmetry analogues of trimesic acid

The two-dimensional assembly of multicarboxylated arenes is explored at the liquid-graphite interface using scanning tunneling microscopy. Symmetry variations were introduced via phenylene spacer addition and the influence of these perturbations on the formation of hydrogen-bonded motifs from an alkanoic acid solvent is observed. This work demonstrates the importance of symmetry in 2D crystal formation and draws possible links of this behavior to prediction of coordination modes in three-dimensional coordination polymers.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.

Discovery of trifluoromethyl(pyrimidin-2-yl)azetidine-2-carboxamides as potent, orally bioavailable TGR5 (GPBAR1) agonists: Structure-activity relationships, lead optimization, and chronic in vivo efficacy

Activation of the G-protein coupled receptor (GPCR) Takeda G-protein receptor 5 (TGR5), also known as G-protein bile acid receptor 1 (GPBAR1), has been shown to play a key role in pathways associated with diabetes, metabolic syndrome, and autoimmune disease. Nipecotamide 5 was identified as an attractive starting point after a high-throughput screen (HTS) for receptor agonists. A comprehensive hit-to-lead effort culminated in the discovery of 45h as a potent, selective, and bioavailable TGR5 agonist to test in preclinical metabolic disease models. In genetically obese mice (ob/ob), 45h was as effective as a dipeptidyl peptidase-4 (DPP-4) inhibitor at reducing peak glucose levels in an acute oral glucose tolerance test (OGTT), but this effect was lost upon chronic dosing.