[3-(ethoxycarbonyl)phenyl]boronic acid

• ChemBase ID: 10037
• Molecular Formular: C9H11BO4
• Molecular Mass: 193.99224
• Monoisotopic Mass: 194.07503923
• SMILES: c1cc(cc(c1)B(O)O)C(=O)OCC
• Canonical SMILES: CCOC(=O)c1cccc(c1)B(O)O
• InChI: InChI=1S/C9H11BO4/c1-2-14-9(11)7-4-3-5-8(6-7)10(12)13/h3-6,12-13H,2H2,1H3
• InChIKey: REHVCPNQQBDOJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(ethoxycarbonyl)phenyl]boronic acid
• IUPAC Traditional name: 3-(ethoxycarbonyl)phenylboronic acid
• Synonyms: Ethyl 3-boronobenzoate; 3-(Ethoxycarbonyl)benzeneboronic acid; 3-Ethoxycarbonylphenylboronic acid; 3-Carboethoxyphenylboronic acid; 3-Ethoxycarbonylphenylboronic acid; 3-乙氧羰基苯硼酸

Database IDs

• CAS Number: 4334-87-6
• MDL Number: MFCD02179444
• PubChem SID: 160973344; 24880751
• PubChem CID: 3249312

CALCULATED PROPERTIES

• Acid pKa: 8.573594
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.1295354
• LogD (pH = 7.4): 2.1018631
• Log P: 2.1299
• Molar Refractivity: 47.3774 cm^3
• Polarizability: 19.81067 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 135-139 °C(lit.); 135-139°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Linear Formula: C2H5OCOC6H4B(OH)2

DETAILS

Sigma Aldrich - 574651

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Palladium-catalyzed Suzuki-Miyaura coupling1,2
• Palladium-catalyzed arylation of aldehydes3
• Reductive cross coupling reactions4
• Preparation of β3-adrenergic receptor agonist5
• Transmetalation reactions6