68716-48-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene is used as a key intermediate in the synthesis of [(pyrimidoindolyl)phenyl]benzamide derivatives and analogs, which are known as Janus kinase inhibitors. These inhibitors are important in the development of treatments for various diseases, including inflammatory and autoimmune disorders, as they help regulate the immune system by targeting specific enzymes involved in cell signaling pathways.
Used in Organic Synthesis:
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene is also used as a versatile building block in organic synthesis for the preparation of a wide range of chemical compounds. Its unique structure allows for various chemical reactions, such as cross-coupling reactions, which enable the formation of new carbon-carbon or carbon-heteroatom bonds. This makes it a valuable component in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-6-5-7-10(8-9)14(15)16/h5-8H,1-4H3

Upstream product

• 25240-59-9 pinacolboronic acid 
• 32578-25-9 trifluoromethanesulfonic acid 3-nitrophenyl ester 
• 585-79-5 m-nitrobromobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13331-27-6 m-nitrobenzene boronic acid 
• 99-09-2 3-nitro-aniline 
• 98-95-3 nitrobenzene 
• 24163-36-8 3,3'-dinitrodiphenyliodonium bromide 
• 121-73-3 3-Nitrochlorobenzene 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 4783-68-0 2-phenoxypyridine 
• 28355-48-8 2-(3-nitrophenoxy)pyridine 

Downstream Products

• 585-79-5 m-nitrobromobenzene 
• 554-84-7 meta-nitrophenol 
• 1036377-14-6 6-methyl-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide 
• 1036377-00-0 6-chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide 
• 1516-59-2 3-nitrophenyl azide 
• 1234215-30-5 1-(hex-1-en-3-yl)-3-nitrobenzene 
• 1400221-08-0 C₁₆H₁₄N₄O₂ 
• 645-00-1 m-iodonitrobenzene 
• 619-24-9 3-nitrobenzonitrile 
• 939430-30-5 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine 
• 93324-67-5 3-([1,1′-biphenyl]-3-yl)pyridine 
• 1565857-85-3 C₂₀H₂₃BO₃ 
• 1345508-91-9 3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-carbonitrile 
• 22868-33-3 2-(3-nitrophenyl)benzothiazole 

Relevant academic research and scientific papers

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

A directing group-assisted ruthenium-catalyzed approach to access: Meta -nitrated phenols

meta-Selective C-H nitration of phenol derivatives was developed using a Ru-catalyzed σ-activation strategy. Cu(NO3)2·3H2O was employed as the nitrating source, whereas Ru3(CO)12 was found to be the most suitable metal catalyst for the protocol. Mechanistic studies suggested involvement of an ortho-CAr-H metal intermediate, which promoted meta-electrophilic aromatic substitution and silver-assisted free-radical pathway.

Redox reactions of small organic molecules using ball milling and piezoelectric materials

Over the past decade, photoredox catalysis has harnessed light energy to accelerate bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be dev

Method for preparing aryl boronate at room temperature

The invention discloses a method for preparing aryl boronate represented by a formula I at a room temperature. The method comprises: carrying out a reaction on a diboron compound represented by a formula II and an aryl halide in an organic solvent for 0.5-8 h at a room temperature under the actions of an alkali, a chloro(2-dicyclohexylphosphino-2',4',6'-tri-isopropyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium (II) catalyst and a 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl ligand, and carrying out post-treatment to obtain the corresponding aryl boronate. According to the present invention, the method has characteristics of mild reaction conditions, simple operation, wide application range, good compatibility with various functional groups on aryl, high efficiency and economy, can achieve high yield of aryl borate under normal pressure and normal pressure conditions, and is suitable for large-scale preparation of aryl borate. The formulas I and II are defined in the specification, wherein R' represents any one selected from phenyl with substituent, pyridyl, thienyl, indyl, pyrazolyl and naphthyl.

Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light

We developed a photocatalyst-free and additive-free, visible light induced borylation reaction using arylazo sulfones as starting material. This protocol shows some advantages such as mild conditions, simple equipment, and wide substrate scope, which gives a complementary protocol for the preparation of arylboronates.

Room-temperature borylation and one-pot two-step borylation/Suzuki-Miyaura cross-coupling reaction of aryl chlorides

A highly efficient room-temperature borylation strategy of aryl chlorides is described. Utilizing Buchwald's second-generation preformed catalyst, boronate esters were obtained for a wide range of substrates in high yield. The method was also applied to Suzuki-Miyaura cross-coupling reaction in a one-pot two-step sequential manner, providing a facile and convenient access to the direct synthesis of biaryl compounds from aryl chlorides.

Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions

Solvent-free protocols for Miyaura borylation and the one-pot, two-step homocoupling of aryl halides are reported for the first time. Bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] is an optimal source of palladium for Miyaura borylation, while for one-pot two-step homocoupling palladium(II) acetate [Pd(OAc)2] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.