(2,6-dimethylphenyl)boronic acid

• ChemBase ID: 32616
• Molecular Formular: C8H11BO2
• Molecular Mass: 149.98274
• Monoisotopic Mass: 150.08520999
• SMILES: c1(c(cccc1C)C)B(O)O
• Canonical SMILES: OB(c1c(C)cccc1C)O
• InChI: InChI=1S/C8H11BO2/c1-6-4-3-5-7(2)8(6)9(10)11/h3-5,10-11H,1-2H3
• InChIKey: ZXDTWWZIHJEZOG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2,6-dimethylphenyl)boronic acid
• IUPAC Traditional name: 2,6-dimethylphenylboronic acid
• Synonyms: 2,6-Dimethylbenzeneboronic acid; 2,6-Xyleneboronic acid; 2,6-Xylylboronic acid; 2,6-Dimethylphenylboronic acid; 2-Borono-1,3-dimethylbenzene; 2-Borono-m-xylene; 2,6-Dimethylbenzeneboronic acid 97%; 2,6-Dimethylphenylboronic acid; 2,6-Dimethylphenylboronic acid; 2,6-Dimethylbenzeneboronic acid; 2,6-二甲基苯硼酸

Database IDs

• CAS Number: 100379-00-8
• MDL Number: MFCD01009693
• PubChem SID: 24871544; 160995923
• PubChem CID: 583322

CALCULATED PROPERTIES

• Acid pKa: 8.89208
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.574025
• LogD (pH = 7.4): 2.560508
• Log P: 2.5742
• Molar Refractivity: 40.6859 cm^3
• Polarizability: 17.06502 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 105 °C (dec.)(lit.); 105°C; 120--124°C; 120-126°C dec.

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0%; 97%; 98%
• Impurities: <10% water
• Linear Formula: (CH3)2C6H3B(OH)2

DETAILS

Sigma Aldrich - 480061

Other Notes
contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle
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 biarylalanines tetrapeptide libraries9
• Protein Kinase inhibitors10