380151-86-0

Basic information

• Product Name: 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE
• Synonyms: 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE;3-FORMYLPHENYLBORONIC ACID, PINACOL ESTER;2-dioxaborolan-2-yl)-benzaldehyde;3-Formylbenzeneboronic acid, pinacol ester;Benzaldehyde, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;3-FormylPhenylboronic acid neopentyl ester pinacol ester
• CAS NO: 380151-86-0
• Molecular Formula: C₁₃H₁₇BO₃
• Molecular Weight: 232.08
• Mol File: 380151-86-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: 50-54°C
• Boiling Point: 345.1°Cat760mmHg
• Flash Point: 162.5°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 6.28E-05mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE(380151-86-0)
• EPA Substance Registry System: 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE(380151-86-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 380151-86-0(Hazardous Substances Data)

Usage

General Description

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde is a chemical compound with the molecular formula C15H19BO2. It is a benzaldehyde derivative containing a boron-dioxaborolane moiety. 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE is often used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. It is commonly employed in the Suzuki-Miyaura coupling reaction, a widely used method for the construction of complex organic molecules. 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE is highly valuable in the field of chemical research and pharmaceutical development due to its versatile reactivity and ability to facilitate the formation of important chemical bonds.

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

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 87199-16-4 3-Formylphenylboronic acid 
• 619-21-6 m-formylphenyl benzoic acid 
• 73183-34-3 bis(pinacol)diborane 
• 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 
• 3132-99-8 m-bromobenzoic aldehyde 

Downstream Products

• 439090-71-8 C₆H₄NCOC₆H₄BO₂C(CH₃)2C(CH₃)2 
• 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 
• 883738-19-0 1,1-dimethylethyl 4-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1-piperazinecarboxylate 
• 946168-04-3 2-(3-ethynylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Relevant articles and documents

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.

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.