380151-86-0

Usage

Uses

Used in Organic Synthesis:
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde is utilized as a reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds. Its boron-dioxaborolane group plays a crucial role in facilitating these bond formations, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its versatility in forming different types of chemical bonds allows for the creation of a wide range of drug candidates with potential therapeutic applications.
Used in the Suzuki-Miyaura Coupling Reaction:
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde is particularly important in the Suzuki-Miyaura coupling reaction, a widely used method for constructing complex organic molecules. This reaction allows for the formation of carbon-carbon bonds between an organoboron compound and an organic halide or triflate, with 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde serving as a precursor to the organoboron compound. This method is highly valuable in the synthesis of biologically active compounds and advanced materials.

InChI:InChI=1/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-6-10(8-11)9-15/h5-9H,1-4H3

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 73183-34-3 bis(pinacol)diborane 
• 619-21-6 m-formylphenyl benzoic acid 
• 622-29-7 N-Benzylidenemethylamine 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 6852-58-0 N-benzylidene tert-butylamine 
• 100-52-7 benzaldehyde 
• 1448723-41-8 C₂₅H₃₃BN₂O₇S 
• 1448723-42-9 C₂₀H₂₅BN₂O₅S 
• 269409-73-6 3-carboxyphenylboronic acid pinacol ester 
• 587-04-2 m-Chlorobenzaldehyde 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 87199-16-4 3-Formylphenylboronic acid 

Downstream Products

• 946168-04-3 2-(3-ethynylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 1189170-88-4 5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 439090-71-8 C₆H₄NCOC₆H₄BO₂C(CH₃)2C(CH₃)2 
• 1415694-93-7 (S)-2-(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzylamino)ethanol hydrochloride 
• 269410-09-5 (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine 
• 443776-76-9 (3‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)methanol 
• 1544673-86-0 N-cyclohexyl-2-phenyl-2-{N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]acetamido}acetamide 
• 1544674-00-1 [3-({N-[2-(cyclohexylamino)-2-oxo-1-phenylethyl]acetamido}methyl)phenyl]boronic acid 
• 1544674-08-9 2-[N-([1,1'-biphenyl]-3-ylmethyl)acetamido]-N-cyclohexyl-2-phenylacetamide 
• 214360-75-5 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]isoindoline-1,3-dione 

Relevant academic research and scientific papers

2-thioxothiazolidin-4-one analogs as pan-pim kinase inhibitors

Proviral integration site for Moloney murine leukemia virus (PIM) kinases are proto-oncogenic kinases involved in the regulation of several cellular processes. PIM kinases are promising targets for new drug development because they play a major role in many cancer-specific pathways, such as survival, apoptosis, proliferation, cell cycle regulation, and migration. Here, 2-thioxothiazolidin-4-one derivatives were synthesized and evaluated as potent pan-PIM kinase inhibitors. Optimized compounds showed single-digit nanomolar IC50 values against all three PIM kinases with high selectivity over 14 other kinases. Compound 17 inhibited the growth of Molm-16 cell lines (EC50 = 14 nM) and modulated the expression of pBAD and p4EBP1 in a dose-dependent manner.

Development of Potent PfCLK3 Inhibitors Based on TCMDC-135051 as a New Class of Antimalarials

The protein kinase PfCLK3 plays a critical role in the regulation of malarial parasite RNA splicing and is essential for the survival of blood stage Plasmodium falciparum. We recently validated PfCLK3 as a drug target in malaria that offers prophylactic,

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.

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.

New cyanopyridine based conjugative polymers as blue emitters: Synthesis, photophysical, theoretical and electroluminescence studies

Herein, we report the design of three new blue light emitting conjugated polymers (Th-Py-1, Th-Py-2 and Th-Py-3), carrying cyanopyridine ring as a strong electron accepting unit and thiophene as well as phenylene vinylene scaffolds with different substituents, as electron donating moieties. The newly designed monomers/polymers were synthesized using well-known synthetic protocols such as cyclocondensation, O-alkylation, Suzuki cross coupling, Wittig and Knoevenagel reactions. They were well-characterized by spectral, thermal, photophysical, electrochemical and gel permeation chromatography (GPC) techniques. Further, they were subjected to theoretical studies using DFT simulations, performed at B3LYP/TZVP level using Turbomole 7.2 V software package. The new polymers were tested in PLED devices (ITO/PEDOT: PSS/Polymer/Al) as emissive materials. Optical studies revealed that, all the polymers displayed light absorption in the range of 377–397 nm and blue light emission in the order of 432–482 nm, respectively. Further, their band-gaps were calculated to be in the order of 2.55–2.64 eV using both optical and electrochemical data. Furthermore, the TGA study indicated that, they possess good thermal stability with onset decomposition temperature, greater than 300 ?C under nitrogen atmosphere. Interestingly, use of these polymers in new PLEDs as emissive layers, has shown improved performance when compared to previously reported polymers in similar type of devices. They show blue light emission with a low threshold voltage of 3.5–3.9 V, affirming an efficient electron injection in the diodes.

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

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.

Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines

The ligand-enabled development of ortho and meta C-H borylation of aromatic aldehydes is reported. It was envisaged that while ortho borylation could be achieved using tert-butylamine as the traceless protecting/directing group, meta borylation proceeds via an electrostatic interaction and a secondary interaction between the ligand of the catalyst and the substrate. These ligand-substrate electrostatic interactions and secondary B-N interactions provide an unprecedented controlling factor for meta-selective C-H activation/borylation.

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.