(3,5-dimethoxyphenyl)boronic acid

• ChemBase ID: 32763
• Molecular Formular: C8H11BO4
• Molecular Mass: 181.98154
• Monoisotopic Mass: 182.07503923
• SMILES: c1(cc(cc(c1)B(O)O)OC)OC
• Canonical SMILES: COc1cc(OC)cc(c1)B(O)O
• InChI: InChI=1S/C8H11BO4/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5,10-11H,1-2H3
• InChIKey: XUIURRYWQBBCCK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3,5-dimethoxyphenyl)boronic acid
• IUPAC Traditional name: 3,5-dimethoxyphenylboronic acid
• Synonyms: 3,5-Dimethoxyphenylboronic acid; 3,5-Dimethoxybenzeneboronic acid; 3,5-Dimethoxyphenylboronic acid; 3,5-二甲氧基苯硼酸

Database IDs

• CAS Number: 192182-54-0
• MDL Number: MFCD03095127
• PubChem SID: 160996070
• PubChem CID: 4374257

CALCULATED PROPERTIES

• Acid pKa: 8.556511
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.1340209
• LogD (pH = 7.4): 1.1052752
• Log P: 1.1344
• Molar Refractivity: 43.5299 cm^3
• Polarizability: 18.586714 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 202-207 °C; 272-276°C
• Flash Point: 177.8 °F; 81 °C

Safety Information

• Storage Warning: IRRITANT, KEEP COLD; Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Purity: ≥95%; 98%
• Empirical Formula (Hill Notation): C8H11BO4

DETAILS

Sigma Aldrich - 715271

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Palladium-catalyzed coupling reactions1
• Preparation of benzopyranone derivatives as positive GABAA receptor modulators2
• Preparation of aryl alkenes via three-component coupling catalyzed by palladium3
• Suzuki-Miyaura coupling4
• Rhodium catalyzed cyanation with N-cyano-N-phenyl-p-methylbenzenesulfonamide5
• Preparation of bisphosphonate inhibitors of human farnesyl pyrophosphate synthase6