[2-(ethoxycarbonyl)phenyl]boronic acid

• ChemBase ID: 32704
• Molecular Formular: C9H11BO4
• Molecular Mass: 193.99224
• Monoisotopic Mass: 194.07503923
• SMILES: c1(c(cccc1)C(=O)OCC)B(O)O
• Canonical SMILES: CCOC(=O)c1ccccc1B(O)O
• InChI: InChI=1S/C9H11BO4/c1-2-14-9(11)7-5-3-4-6-8(7)10(12)13/h3-6,12-13H,2H2,1H3
• InChIKey: QZKVVOXAEBCLPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(ethoxycarbonyl)phenyl]boronic acid
• IUPAC Traditional name: 2-(ethoxycarbonyl)phenylboronic acid
• Synonyms: 2-Ethoxycarboxyphenylboronic acid; (2-Ethoxycarbonylphenyl)boronic acid; 2-(Ethoxycarbonyl)phenylboronic acid; Ethyl 2-boronobenzoate; 2-(Ethoxycarbonyl)benzeneboronic acid; 2-Ethoxycarbonylphenylboronic acid; 2-(ethoxycarbonyl)phenylboronic acid; 2-(乙氧羰基)苯硼酸

Database IDs

• CAS Number: 380430-53-5
• MDL Number: MFCD02179453
• PubChem SID: 160996011
• PubChem CID: 2773405

CALCULATED PROPERTIES

• Acid pKa: 8.210274
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.129059
• LogD (pH = 7.4): 2.0676978
• Log P: 2.1299
• Molar Refractivity: 47.3774 cm^3
• Polarizability: 19.813156 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 128-136 °C; 130-133°C

Safety Information

• Storage Warning: 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

Product Information

• Purity: 97%; 98%
• Linear Formula: CH3CH2O2C(C6H4)B(OH)2

DETAILS

Sigma Aldrich - 683833

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Synthesis of embelin derivatives via Suzuki-Miyaura reaction, cross metathesis and Wittig olefination1
• Asymmetric cyclopropanation of alkenes with di-Me diazomalonate catalyzed by chiral diene-rhodium complexes2
• Preparation of phenylalanines as selective AMPA- and kainate receptor ligands3
• Preparation of aryl pyrazinones via microwave-assisted palladium-catalyzed arylation of resin supported pyrazinones under simultaneous cooling condition4
• Regioselective preparation of (aryl)hydroxyquinolines via Suzuki-Miyaura cross-coupling with chloro(tosyloxy)quinoline under anhydrous conditions followed by nucleophilic deprotection of the tosyl group5