325142-87-8

Usage

Uses

Used in Organic Synthesis:
3-(N,N-Dimethylamino)phenylboronic acid, pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, which are fundamental in constructing complex organic molecules and frameworks.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-(N,N-Dimethylamino)phenylboronic acid, pinacol ester is utilized as a key intermediate in the synthesis of various drug molecules, contributing to the development of new therapeutic agents.
Used in Agrochemical Development:
Similarly, in agrochemicals, 3-(N,N-Dimethylamino)phenylboronic acid, pinacol ester serves as a building block in the creation of compounds that can be used in crop protection and other agricultural applications.
Used in Biological Research:
3-(N,N-Dimethylamino)phenylboronic acid, pinacol ester is used as a tool in biological research for applications such as imaging, where it can help visualize specific biological processes or structures, and sensing, where it may be employed to detect or measure biologically relevant molecules or activities.

InChI:InChI=1/C14H22BNO2/c1-13(2)14(3,4)18-15(17-13)11-8-7-9-12(10-11)16(5)6/h7-10H,1-6H3

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 16518-62-0 3-bromo-N,N-dimethylaniline 
• 6848-13-1 3-chloro-N,N-dimethylaniline 
• 73183-34-3 bis(pinacol)diborane 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 99-64-9 3-(dimethylamino)benzoic acid 
• 99-07-0 3-Dimethylaminophenol 
• 4783-67-9 N,N-dimethyl-3-(pyridin-2-yloxy)aniline 

Downstream Products

• 1450994-20-3 3-(1H-indol-6-yl)-N,N-dimethylaniline 

Relevant academic research and scientific papers

Remote steric control for undirected meta-selective C-H activation of arenes

Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy

Synthesis of fluorenes and their related compounds from biaryls and Meldrum's acid derivatives

A new synthetic method for preparing fluorenes from amino group-containing biaryls and Meldrum's acid derivatives was developed. The reaction proceeded without a catalyst and loss of functional groups. The corresponding six- and seven-membered cyclic prod

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

METHOD FOR SYNTHESIZING BORONATE ESTER COMPOUND, SODIUM SALT OF BORONATE ESTER COMPOUND, AND METHOD FOR SYNTHESIZING THE SAME

An object is to establish a technology with which a boronate ester compound can be easily and efficiently synthesized at a low cost with a small number of steps without the need for a complex chemical method and reagents that need to be carefully handled. A further object is to establish a sodium salt of a boronate ester compound that is a novel compound and a technology for synthesizing the sodium salt of a boronate ester compound. Provided are a sodium salt of a boronate ester compound and a method for synthesizing a boronate ester compound or a sodium salt of a boronate ester compound that includes reacting, in a reaction solvent, an organic chloride with a dispersion product obtained by dispersing sodium in a dispersion solvent to obtain an organic sodium compound, and reacting the obtained organic sodium compound with a borate ester compound to obtain a boronate ester compound or a sodium salt of a boronate ester compound.

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation

Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.

Cobalt-Catalyzed C(sp2)-H borylation with an air-stable, readily prepared terpyridine cobalt(II) Bis(acetate) precatalyst

A bench-stable, 4-aryl-substituted terpyridine supported, high-spin cobalt(II) bis(acetate) complex, (ArTpy)Co- (OAc)2 (ArTpy = 4′-(4-N,N′-dimethylaminophenyl)-2,2′:6′,2″- Terpyridine), is active for the C(sp2)-H borylation of arenes and heteroarenes with B2Pin2 (Pin = pinacolato). Optimization of the catalytic borylation reaction revealed improved performance in the presence of LiOMe and turnover numbers of up to 100 have been observed using all air-stable components. EPR specstroscopy identified formation of inactive cobalt species, promoted by excess HBPin. A high-spin cobalt(II) bis[(diacetoxy)- pinacolatoborate-κ3O,O,O] compound has been isolated and characterized by X-ray diffraction and is the result of catalyst deactivation.

Iron-catalyzed C-H borylation of arenes

Well-defined iron bis(diphosphine) complexes are active catalysts for the dehydrogenative C-H borylation of aromatic and heteroaromatic derivatives with pinacolborane. The corresponding borylated compounds were isolated in moderate to good yields (25-73%) with a 5 mol% catalyst loading under UV irradiation (350 nm) at room temperature. Stoichiometric reactivity studies and isolation of an original trans-hydrido(boryl)iron complex, Fe(H)(Bpin)(dmpe)2, allowed us to propose a mechanism showing the role of some key catalytic species.

Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: Borylative removal of the directing group

The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.

PHOSPHOINOSITIDE 3-KINASE INHIBITORS WITH ZINC BINDING MOIETY

PROBLEM TO BE SOLVED: To provide phosphoinositide 3-kinase inhibitors with a zinc binding moiety. SOLUTION: There is provided a compound represented by formula (I) in the figure. (X is S, O or the like; Y is CH, N or the like; G1 is optionally substituted N or the like; R1 and R2 are each independently H or the like; C is a substituted heterocycle or the like; B is a linear alkyl or the like; Ra and Rb together with the nitrogen atom coupled to them are morpholino or the like; G2 is an indazole ring or the like; q, r and s are independently from 0 to 1, provided that at least one of them is 1; t is from 0 to 1; n is from 0 to 4; and p is from 0 to 2.) COPYRIGHT: (C)2016,JPOandINPIT

An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane

(Chemical Equation Presented) borylation of aryl halides with an inexpensive and atom-economical boron source, pinacol borane, has been developed. This system allows for the conversion of aryl and heteroaryl iodides, bromides, and several chlorides, containing a variety of functional groups, to the corresponding pinacol boronate esters. In addition to the increase in substrate scope, this is the first general method where relatively low quantities of catalyst and short reaction times can be employed.