o-Tolylboronic acid
o-Tolylboronic acid (CAS: 16419-60-6, Formula: CH3C6H4B(OH)2) is a white to off-white solid with a molecular weight of 135.96 g/mol. This organoboron compound serves as a valuable reagent in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions like the Suzuki-Miyaura coupling. Its utility extends to various synthetic transformations, including direct arylation and addition reactions, making it a key building block in pharmaceutical and materials science research.
- IUPAC
- (2-Tolyl)boronic acid,2-Methyl-1-phenylboronic acid,2-Methylbenzeneboronic acid,2-Methylphenylboronic acid,2-Tolueneboronic acid,o-Boronotoluene,o-Methylphenylboronic acid,o-Tolueneboronic acid
- Synonyms
- 2-Methylbenzeneboronic acid2-Tolueneboronic acido-Methylphenylboronic acid(2-Tolyl)boronic acid2-Methylphenylboronic acido-Tolylboronic acid
Suzuki-Miyaura Cross-Coupling
o-Tolylboronic acid is widely employed as a coupling partner in Suzuki-Miyaura reactions, facilitating the formation of carbon-carbon bonds. It is effective in aqueous media and in ligand-free or phosphine-free conditions, offering versatility in synthetic strategies.
Direct Arylation Reactions
This boronic acid participates in palladium-catalyzed direct arylation of heterocycles like pyrazoles. It also serves as a substrate in ruthenium-catalyzed direct arylation processes, expanding its scope in aromatic functionalisation.
Organometallic Reagent
As an organometallic reagent, o-tolylboronic acid is useful in various metal-catalyzed transformations. It has been used in rhodium-catalyzed asymmetric 1,4-addition reactions, contributing to the synthesis of chiral molecules.
Synthesis of Ligands and Catalysts
It is instrumental in the preparation of complex molecules, including chiral monophosphorus ligands for asymmetric catalysis and palladium nanoparticles supported on ionic copolymers for recyclable catalytic systems.
| Molecular weight | 135.96 |
|---|---|
| Linear formula | CH3C6H4B(OH)2 |
| Assay | ≥95.0% |
| Application | Reagent used for• Palladium-catalyzed direct arylation of pyrazoles with phenylboronic acids1 • Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water2 • Ruthenium catalyzed direct arylation reactions3 • Ligand-free copper-catalyzed coupling reactions4 • Copper-catalyzed cross-coupling reactions of diaryl diselenides5 • Phosphine-free Suzuki-Miyaura cross-coupling reactions6 • Rhodium-catalyzed asymmetric 1,4-addition reactions7 Reagent used in Preparation of• Chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction8 • Palladium nanoparticles immobilized by click ionic copolymers as recyclable catalysts for Suzuki-Miyaura cross-coupling reaction in water9 • Human farnesyl pyrophosphate synthase inhibi |
| Melting point | 162-164 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is o-Tolylboronic acid used for?
+
o-Tolylboronic acid is primarily used as a reagent in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, for the formation of carbon-carbon bonds. It also finds application in direct arylation reactions and the synthesis of various organic intermediates and ligands.
What is the CAS number and chemical formula for o-Tolylboronic acid?
+
The CAS number for o-Tolylboronic acid is 16419-60-6, and its chemical formula is CH3C6H4B(OH)2.
What grade and purity does Tech Serve Solutions supply?
+
Tech Serve Solutions supplies o-Tolylboronic acid with an assay of ≥95.0%. We do not represent this product as USP, BP, or EP grade.
How should o-Tolylboronic acid be handled safely?
+
o-Tolylboronic acid is a warning hazardous substance, causing skin irritation (H315), eye irritation (H319), and respiratory irritation (H335). Handle with appropriate personal protective equipment, including a dust mask (type N95), eyeshields, and gloves. Ensure adequate ventilation and avoid breathing dust. In case of contact, follow P261 and P305 + P351 + P338.
Is o-Tolylboronic acid a controlled substance?
+
The provided data does not indicate that o-Tolylboronic acid is a controlled substance.
How is o-Tolylboronic acid packed and exported?
+
o-Tolylboronic acid is carefully packaged to maintain its integrity during transit. Tech Serve Solutions is experienced in exporting fine chemicals globally, adhering to all necessary regulations.
How can I request a sample or quote for o-Tolylboronic acid?
+
To request a sample or a quote for o-Tolylboronic acid, please contact our sales team through the provided channels on our website, specifying your requirements.
▶ Related products
1-(2-Fluorobenzyl)piperazine
C11H15FN2
Chemical Synthesis
1-(2-Fluorophenyl)biguanide hydrochloride
Chemical Synthesis
1-(2-Fluorophenyl)cyclopropanecarboxylic acid
C10H9FO2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine
C10H13FN2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine monohydrochloride
C10H13FN2 · HCl
Chemical Synthesis
1-(2-Furoyl)-1H-benzotriazole
C11H7N3O2
Chemical Synthesis
1-(2-Furoyl)piperazine
C9H12N2O2
Chemical Synthesis
1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione
Chemical Synthesis
▶ Explore more
3-Methyl-1,5-di-p-tolyl-1,4-pentazadiene
Chemical Synthesis
3-Methyl-1,5-pentanediol
Chemical Synthesis
3-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine
C11H13N3
Chemical Synthesis
3-Methyl-1-(3′-sulfoamidophenyl)-5-pyrazolone
C10H11N3O3S
Chemical Synthesis