100379-00-8

Basic information

• Product Name: 2,6-Dimethylphenylboronic acid
• Synonyms: 2,6-DIMETHYLPHENYLBORONIC ACID;2,6-DIMETHYLBENZENEBORONIC ACID;AKOS BRN-0223;RARECHEM AH PB 0195;2,6-Dimethylphenylboronic;2,6-Dimethylbenzeneboronic acid 97%;2,6-Dimethylphenylboronic Acid (contains varying amounts of Anhydride);m-Xylene-2-boronic Acid
• CAS NO: 100379-00-8
• Molecular Formula: C₈H₁₁BO₂
• Molecular Weight: 149.98
• Product Categories: blocks;BoronicAcids;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic acid;Boronic Acids;Boronic Acids and Derivatives;6
• Mol File: 100379-00-8.mol

Chemical Properties

• Melting Point: 105 °C (dec.)(lit.)
• Boiling Point: 299.9 °C at 760 mmHg
• Flash Point: 135.2 °C
• Appearance: White/Crystalline Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 0.000838mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: 0-6°C
• Solubility: Soluble in methanol.
• PKA: 8.68±0.58(Predicted)
• CAS DataBase Reference: 2,6-Dimethylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethylphenylboronic acid(100379-00-8)
• EPA Substance Registry System: 2,6-Dimethylphenylboronic acid(100379-00-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 100379-00-8(Hazardous Substances Data)

Usage

Uses

Used in Suzuki Reaction:
2,6-Dimethylphenylboronic acid is used as a reagent for palladium-catalyzed Suzuki-Miyaura coupling reactions, which are widely employed in the synthesis of various organic compounds, including pharmaceuticals and natural products. It facilitates the formation of carbon-carbon bonds, making it a valuable tool in organic chemistry.
Used in Pd-Catalyzed Homocouplings:
2,6-Dimethylphenylboronic acid is also utilized in palladium-catalyzed homocouplings, a type of chemical reaction that involves the coupling of two identical molecules to form a larger molecule. This process is particularly useful in the synthesis of complex organic molecules.
Used in Rhodium(I)-Catalyzed 1,4-Addition Reactions:
2,6-Dimethylphenylboronic acid is employed in rhodium(I)-catalyzed 1,4-addition reactions, which are important in the synthesis of conjugated dienes and other unsaturated compounds. These reactions are crucial for the production of various chemicals and materials.
Used in the Preparation of Protein Kinase Inhibitors:
2,6-Dimethylphenylboronic acid is used in the preparation of protein kinase inhibitors, which are essential in the development of drugs targeting various diseases, including cancer and inflammatory conditions. Protein kinases are enzymes that play a significant role in cellular signaling pathways, and their inhibition can help regulate these pathways.
Used in the Preparation of G Protein-Coupled Receptor:
2,6-Dimethylphenylboronic acid is also used in the preparation of G protein-coupled receptors (GPCRs), which are a large family of proteins involved in various cellular processes. These receptors are important drug targets for treating a wide range of diseases, including neurological disorders, cardiovascular diseases, and metabolic conditions.

InChI:InChI=1/C8H11BO2/c1-6-3-4-8(9(10)11)7(2)5-6/h3-5,10-11H,1-2H3

Upstream product

• 121-43-7 Trimethyl borate 
• 21450-64-6 (2,6-dimethylphenyl)magnesium bromide 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 576-22-7 2-Bromo-m-xylene 
• 13675-18-8 tetrahydroxydiboron 
• 7732-18-5 water 
• 139719-91-8 dimethoxy(2,6-dimethylphenyl)borone 

Downstream Products

• 157402-43-2 3-(2,6-dimethyl-phenyl)-pyridine 
• 192182-16-4 2-{2-[2-(2,6-Dimethyl-phenyl)-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione 
• 193087-06-8 2-(2,6-dimethylphenyl)thioxanthen-9-one 
• 147424-62-2 1-(2,6-dimethylphenyl)naphthalene 
• 433222-68-5 3-bromo-2-(2,6-dimethyl)phenylbenzo[b]thiophene 
• 22682-41-3 2,4',6-trimethylbenzophenone 
• 428514-87-8 (R)-1-[6-(2,6-dimethylphenyl)pyridin-2-yl]ethanol 
• 486397-33-5 3-(2,6-dimethyl-phenyl)-cyclohexanone 
• 596819-81-7 2,6-bis(2',6'-dimethylphenyl)pyrazine 

Relevant articles and documents

Concave reagents+. New 2′-substituted m-terphenyls

New 2′-substituted 2,2″,6,6″-tetramethyl-1,1′: 3′,1″-terphenyls have been synthesized. Solubility of concave acids 4b-6b could be enhanced by substitution in 4 and 4″ position, allowing the study of hydrogen-bonded heterodimers. Concave acids show larger

Suppressing π-π Stacking interactions for enhanced solid-state emission of flat aromatic molecules: Via edge functionalization with picket-fence-type groups

Polycyclic aromatic hydrocarbons (PAHs) are promising for materials science because of their high thermal and chemical stability, electron mobility, and unique photophysical properties. However, flat PAHs have limited applications owing to the low processability of their solutions, which originates from the strong π-π interaction between the aromatic rings. Herein, we report an effective method to suppress the π-π stacking of flat and large PAHs through steric hindrance. A 2,6-dimethylphenyl group, which is referred to as the picket-fence (PF) group based on its fence-like shape, was introduced on the edge of hexa-peri-hexabenzocoronene (HBC) through a bottom-up synthetic process. The PF group enhanced the solubility of HBC, while the unique photophysical properties of the core structure were preserved even in the solid state. The steric effect of the PF group is also demonstrated with other flat PAHs, which show excellent solid-state photophysical properties after functionalization with the PF group. Experimental and theoretical results indicate that the picket size plays a critical role in adjusting the PF effect. Furthermore, we fabricated the first organic light-emitting diode (OLED) that uses an HBC-based emitter, and the solid-state emission spectrum of the device is almost the same as that of the emitter in solution. This is possibly due to the maintenance of their morphology without aggregation due to the PF effect. Moreover, the full width at half maximum of the electroluminescence band was very narrow at only 20 nm. This journal is

Photophysical properties of structural isomers of homoleptic Ir-complexes derived from xylenyl-substituted N-heterocyclic carbene ligands

The phosphorescence properties of fac-Ir(pmp)3, mer-Ir(pmp)3, fac-Ir(dmpmp)3 and mer-Ir(dmpmp)3 (where pmp = 3-methyl-1-phenyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine and dmpmp = 1-(2′,6′-dimethylbiphenyl-2-yl)-3-

Aryl boronic acid preparation method

The invention belongs to the technical field of fine chemical engineering, and relates to an aryl boronic acid preparation method. In the prior art, aryl boronic acid as a novel safe and environmentally-friendly arylation reagent is widely used in scientific research and production of various fine chemicals containing aryl structures in the fields of medicines, pesticides, advanced materials and the like; and the aryl boronic acid compound preparation method reported in the disclosed literature has problems of harsh reaction conditions and high cost. A purpose of the invention is to provide amethod, wherein an aryl boron compound is formed by carrying out a reaction on a Grignard reagent and trialkyl borate under mild conditions, the composition of the aryl boron compound is converted from the main component diaryl borate into the main component aryl borate, and the aryl borate is hydrolyzed to obtain aryl boric acid, so that the preparation cost of the acyl aryl boric acid compound can be remarkably reduced, and the method has good practical application prospect.

An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10

An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Synthesis of substituted azulenes via Pt(II)-Catalyzed ring-expanding cycloisomerization

Substituted azulenes, valuable structures for electronic devices and pharmaceuticals, have been synthesized by the platinum(II)-catalyzed intramolecular ring-expanding cycloisomerization of 1-en-3-yne with ortho-disubstituted benzene. This novel method provides an alternative route for the efficient synthesis of substituted azulenes. The reaction mechanism of selected catalytic transformations was explored using density functional calculations.

Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand

The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh) 3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by Hbonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′- and 8,8′-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7′-positions have the biggest impact in a positive direction. VANOL destination: The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate; see figure) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Copyright

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.