5980-97-2

Basic information

• Product Name: 2,4,6-Trimethylphenylboronic acid
• Synonyms: MESITYLBORONIC ACID;RARECHEM AH PB 0155;Mesitylboronic acid~2,4,6-Trimethylphenylboronic acid;2,4,6-TRIMETHYLBORONIC ACID;2,4,6-Trimethylbenzeneboronic acid, Mesitylene-2-boronic acid;2,4,6-Trimethylphenylboronic acid,95%;2,4,6-Trimethylpheny;Mesitylene-2-boronic acid
• CAS NO: 5980-97-2
• Molecular Formula: C₉H₁₃BO₂
• Molecular Weight: 164.01
• Product Categories: Boronic acids;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic acid
• Mol File: 5980-97-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 115-122 °C(lit.)
• Boiling Point: 309.1 °C at 760 mmHg
• Flash Point: 140.7 °C
• Appearance: Off-white cryst
• Density: 1.05 g/cm³
• Vapor Pressure: 0.000282mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 9.00±0.58(Predicted)
• BRN: 2831927
• CAS DataBase Reference: 2,4,6-Trimethylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trimethylphenylboronic acid(5980-97-2)
• EPA Substance Registry System: 2,4,6-Trimethylphenylboronic acid(5980-97-2)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-10
• Safety Statements: 37/39-26-33-29-16-3/7/9-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5980-97-2(Hazardous Substances Data)

Usage

Description

2,4,6-Trimethylphenylboronic acid is an organic compound with the molecular formula C9H13BO2. It is an off-white crystalline solid that is commonly used as a reagent in various chemical reactions due to its unique chemical properties.

Uses

Used in Suzuki Reaction:
2,4,6-Trimethylphenylboronic acid is used as a reactant in the Suzuki reaction for the formation of carbon-carbon bonds. The Suzuki-Miyaura coupling is a widely employed method in organic chemistry for the synthesis of biaryl compounds, which are important structural elements in many pharmaceuticals, agrochemicals, and materials.
Used in Cross-coupling with α-bromocarbonyl compounds or 2,6-disubstituted bromoarenes:
2,4,6-Trimethylphenylboronic acid is used as a reactant in cross-coupling reactions with α-bromocarbonyl compounds or 2,6-disubstituted bromoarenes. These reactions are crucial for the synthesis of complex organic molecules and have applications in the development of new drugs and advanced materials.
Used in Synthesis of Biphenyl Arsine Ligands:
2,4,6-Trimethylphenylboronic acid is used as a starting material in the synthesis of biphenyl arsine ligands. These ligands are essential components in various homogeneous catalysts, which are used in a range of chemical reactions, including hydrogenation, hydroformylation, and olefin polymerization.
Used in Addition Reactions to Naphthyridine N-oxides or β-aryloxyacrylates:
2,4,6-Trimethylphenylboronic acid is used as a reactant in addition reactions with naphthyridine N-oxides or β-aryloxyacrylates. These reactions are important for the synthesis of complex heterocyclic compounds, which have potential applications in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C9H13BO2/c1-6-4-7(2)9(10(11)12)8(3)5-6/h4-5,11-12H,1-3H3

Upstream product

• 121-43-7 Trimethyl borate 
• 2633-66-1 2-mesitylmagnesium bromide 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 7732-18-5 water 
• 150-46-9 triethyl borate 
• 5806-59-7 mesityllithium 
• 90670-76-1 mesityl-bis(triphenylsilyl)borane 
• 34907-53-4 dimethoxy(mesityl)borane 
• 5419-55-6 Triisopropyl borate 
• 108-67-8 1,3,5-trimethyl-benzene 
• 67-56-1 methanol 
• 55124-35-1 diisopropylamine borane 

Downstream Products

• 36600-83-6 tris(mesityl)boroxin 
• 120185-90-2 dibutyl-2,4,6-trimethylbenzeneboronate 
• 32212-16-1 4-(4-chloro-phenyl)-2-(2,4,6-trimethyl-phenyl)-2,3-dihydro-[1,3,5,2]oxadiazaborole 
• 32230-14-1 6-bromo-2-(2,4,6-trimethyl-phenyl)-2,3-dihydro-1H-benzo[1,3,2]diazaborinin-4-one 
• 32230-42-5 4-[2-(2,4,6-trimethyl-phenyl)-2,3-dihydro-[1,3,5,2]oxadiazaborol-4-yl]-pyridine 
• 109311-77-5 2-mesityl-1.3-dihydro-2.1.3-benzo diaza borol 
• 1024-64-2 (2,4,6-trimethylphenyl)-(2-methylphenyl)-methanone 
• 39117-68-5 2,4,6-trimethyl-4'-nitro-1,1'-biphenyl 
• 207461-16-3 2-chloro-9-mesityl-1,10-phenanthroline 
• 192226-54-3 2,9-dimesityl-[1,10]-phenanthroline 
• 233770-32-6 2-formyl-3-mesityl-1-tosylpyrrole 
• 954-16-5 2,4,6-Trimethylbenzophenon 
• 225916-84-7 6,6'-bis(2,4,6-trimethylphenyl)-2,2'-bipyridine 
• 89970-02-5 2,2',4,6-tetramethylbiphenyl 

Relevant articles and documents

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area

The perylene diimide substituented by thiophene rings at bay area shows photoactivity and can be used as a photo sensor, but another one substituented by mestylene groups is photostable. The single crystal of 1,7-mesitylene perylene diimide was obtained. X-ray diffraction data of the crystal revealed that the plane of the perylene core was hardly twisted by introduction of mesitylene groups. These mestylene groups are like clips maintaining the planarity of the perylene core. Density functional theory calculation was applied to study the difference of photophysical and photochemical properties. The discovery is valuable for design guidance of perylene diimides.

Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges

A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.