p-Tolylboronic acid
p-Tolylboronic acid (CAS: 5720-05-8), with the molecular formula CH3C6H4B(OH)2 and a molecular weight of 135.96 g/mol, is a key organoboron compound. It serves as a versatile reagent in organic synthesis, predominantly employed in palladium-catalyzed cross-coupling reactions. Its utility extends to various arylation and amidation processes, making it an important building block in the synthesis of complex organic molecules for research and development.
- IUPAC
- (p-Methylphenyl)boronic acid,4-Methylbenzeneboronic acid,4-Methylphenylboronic acid,4-Tolueneboronic acid,4-Tolylboronic acid,p-Tolueneboronic acid,NSC 62870,p-Methylbenzeneboronic acid
- Synonyms
- 4-Methylbenzeneboronic acid4-Methylphenylboronic acidp-Tolueneboronic acid4-Tolylboronic acidp-Methylbenzeneboronic acid(p-Methylphenyl)boronic acid4-Tolueneboronic acidp-Methylphenylboronic acid
Palladium-Catalyzed Cross-Coupling Reactions
p-Tolylboronic acid is extensively used as a coupling partner in Suzuki-Miyaura cross-coupling reactions. It facilitates the formation of carbon-carbon bonds, enabling the synthesis of biaryl compounds and other substituted aromatic systems.
Direct Arylation and C-H Functionalization
This boronic acid participates in direct arylation reactions, including Palladium (Pd)-catalyzed direct arylation and Ruthenium-catalyzed direct arylation. It also finds application in tandem-type Pd(II)-catalyzed oxidative Heck reactions and intramolecular C-H amidation sequences.
Organometallic Synthesis
It is employed in various organometallic transformations, such as cyclopalladation, and in ligand-free copper-catalyzed cross-coupling reactions. Rhodium-catalyzed asymmetric conjugate addition is another area of its application.
Synthesis of Catalysts and Ligands
p-Tolylboronic acid is used in the preparation of catalysts, including those for Suzuki-Miyaura cross-coupling of aryl bromides, and potentially in the synthesis of specialized organic ligands.
| Molecular weight | 135.96 |
|---|---|
| Linear formula | CH3C6H4B(OH)2 |
| Assay | 97% |
| Application | Reagent used for• Palladium (Pd)-catalyzed direct arylation1• Direct Palladium(II)-Catalyzed Synthesis2• Palladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in water3• Cyclopalladation4• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence5• Ruthenium catalyzed direct arylation6• Rhodium-catalyzed asymmetric conjugate addition7• Ligand-free copper-catalyzed cross-coupling reactions8• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions9• Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions10Reagent used in Preparation of• Catalysts for Suzuki-Miyaura cross-coupling of aryl bromides4<b |
| Melting point | 256-263 °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 p-Tolylboronic acid used for?
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p-Tolylboronic acid is primarily used as a reagent in various palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura coupling, direct arylation, and Heck reactions. It is also employed in organometallic synthesis and the preparation of catalysts.
What is the CAS number and molecular formula for p-Tolylboronic acid?
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The CAS number for p-Tolylboronic acid is 5720-05-8, and its molecular formula is CH3C6H4B(OH)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies p-Tolylboronic acid with an assay of 97%. We do not represent this product as USP, BP, or EP grade.
What are the safety and handling precautions for p-Tolylboronic acid?
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p-Tolylboronic acid is classified as a Warning substance with hazard statements H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Appropriate personal protective equipment, including a dust mask (N95), eyeshields, and gloves, should be used. Avoid breathing dust and ensure adequate ventilation.
How is p-Tolylboronic acid packed, shipped, and exported?
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p-Tolylboronic acid is carefully packed to ensure its integrity during transit. As a global supplier, Tech Serve Solutions adheres to all necessary regulations for the safe and compliant shipping and export of chemicals worldwide.
How can I request a sample or quote for p-Tolylboronic acid?
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To request a sample or a quotation for p-Tolylboronic acid, please contact our sales department through the website or by phone, providing your specific requirements.
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