2,6-Dimethylphenylboronic acid
2,6-Dimethylphenylboronic acid (CAS 100379-00-8), with the molecular formula (CH3)2C6H3B(OH)2 and a molecular weight of 149.98, is a vital aryl boronic acid derivative. It serves as a key reagent in various palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura couplings, and is instrumental in organic synthesis for preparing complex molecules, notably pharmaceuticals and advanced materials. Its utility extends to one-pot nitration and hydroxylation reactions.
- IUPAC
- 2,6-Dimethylbenzeneboronic acid,2,6-Xyleneboronic acid,2,6-Xylylboronic acid
- Synonyms
- (CH3)2C6H3B(OH)22,6-Dimethylbenzeneboronic acid2,6-Xyleneboronic acid2,6-Xylylboronic acid
Suzuki-Miyaura Coupling Reactions
This compound is a valuable substrate in palladium-catalyzed Suzuki-Miyaura coupling reactions, facilitating the formation of carbon-carbon bonds. It is also employed in expanded copper-assisted Suzuki-Miyaura couplings, even with challenging substrates like aryl chlorides.
Organic Synthesis Reagent
2,6-Dimethylphenylboronic acid is utilized in diverse synthetic transformations. It participates in one-pot ipso-nitration reactions, nickel-catalyzed cross-couplings of chromene acetals, and rhodium(I)-catalyzed 1,4-addition reactions.
Hydroxylation and Coupling Reactions
The reagent is employed in visible-light initiated aerobic oxidative hydroxylation catalyzed by ruthenium complexes. Furthermore, it finds application in palladium-catalyzed homocoupling reactions.
Pharmaceutical Intermediate Synthesis
It plays a role in the preparation of biologically active molecules, such as orally bioavailable G protein-coupled receptor 40 agonists investigated for diabetes treatment, and in the structure-activity relationship studies of antitumor compounds.
| Molecular weight | 149.98 |
|---|---|
| Linear formula | (CH3)2C6H3B(OH)2 |
| Assay | ≥95.0% |
| Impurities tested | <10% water |
| Application | Reagent used for• Palladium catalyzed Suzuki-Miyaura coupling reactions1 • One-pot ipso-nitration of arylboronic acids including broader substrate scope of heterocycles and functional groups2 • Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids3 • Visible-light initiated aerobic oxidative hydroxylation catalyzed by Ru-complex4 • Rhodium(I)-catalyzed 1,4-addition reactions5 • Pd-catalyzed homocouplings6 • Expanded scope of Cu assisted Suzuki-Miyaura coupling reactions including aryl chlorides and polyhalo aryl boronates7 Reagent used in Prepration of• Orally bioavialable G Protein-Coupled Receptor 40 agonists for diabetes treatment8 • Solid phase synthesis and antitumor structure-activity relationship of Smac triazoloprolines and biarylalani |
| Melting point | 105 °C (dec.)(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
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 2,6-Dimethylphenylboronic acid used for?
+
2,6-Dimethylphenylboronic acid is primarily used as a reagent in palladium-catalyzed Suzuki-Miyaura coupling reactions, one-pot ipso-nitration of arylboronic acids, nickel-catalyzed cross-coupling of chromene acetals, visible-light initiated aerobic oxidative hydroxylation, rhodium(I)-catalyzed 1,4-addition reactions, and palladium-catalyzed homocouplings. It is also used in the preparation of pharmaceutical intermediates and biologically active compounds.
What is the CAS number and formula for 2,6-Dimethylphenylboronic acid?
+
The CAS number for 2,6-Dimethylphenylboronic acid is 100379-00-8. Its linear formula is (CH3)2C6H3B(OH)2.
What grade and purity does Tech Serve Solutions supply?
+
Tech Serve Solutions supplies 2,6-Dimethylphenylboronic acid with an assay of ≥95.0%. We do not represent this product as USP, BP, EP, or pharmacopoeia grade.
How should 2,6-Dimethylphenylboronic acid be handled?
+
Handling 2,6-Dimethylphenylboronic acid requires appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter is recommended. The compound is classified with WGK Germany 3, indicating a high hazard to water.
Is 2,6-Dimethylphenylboronic acid a controlled substance?
+
The provided data does not indicate that 2,6-Dimethylphenylboronic acid is a controlled substance.
How is 2,6-Dimethylphenylboronic acid shipped or exported?
+
As a global supplier, Tech Serve Solutions exports fine chemicals. Specific shipping and packaging details for 2,6-Dimethylphenylboronic acid will be provided upon inquiry.
How can I request a sample or quote for 2,6-Dimethylphenylboronic acid?
+
To request a sample or a quote for 2,6-Dimethylphenylboronic acid, please contact our sales team through the website or directly via the provided contact information.
▶ 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