[4-(ethoxycarbonyl)phenyl]boronic acid

• ChemBase ID: 32859
• Molecular Formular: C9H11BO4
• Molecular Mass: 193.99224
• Monoisotopic Mass: 194.07503923
• SMILES: c1(ccc(cc1)C(=O)OCC)B(O)O
• Canonical SMILES: CCOC(=O)c1ccc(cc1)B(O)O
• InChI: InChI=1S/C9H11BO4/c1-2-14-9(11)7-3-5-8(6-4-7)10(12)13/h3-6,12-13H,2H2,1H3
• InChIKey: ZLNFACCFYUFTLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(ethoxycarbonyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(ethoxycarbonyl)phenylboronic acid
• Synonyms: Ethyl 4-boronobenzoate; 4-(Ethoxycarbonyl)benzeneboronic acid; (4-Ethoxycarbonylphenyl)boronic acid; 4-Ethoxy carbonyl phenylboronic acid; 4-Borono-benzoic Acid 1-Ethyl Ester; p-Borono-benzoic Acid 1-Ethyl Ester; 4-(Ethoxycarbonyl)phenylboronic Acid; 4-Ethoxycarbonylphenylboronic acid; 4-Carboethoxybenzeneboronic acid; 4-Boronobenzoic acid 1-ethyl ester; 4-Ethoxycarbonylphenylboronic acid; 4-乙氧羰基苯硼酸; 4-羧酸乙酯苯硼酸

Database IDs

• CAS Number: 4334-88-7
• MDL Number: MFCD02179441
• PubChem SID: 160996166; 24880750
• PubChem CID: 2734350

CALCULATED PROPERTIES

• Acid pKa: 8.510246
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.1294785
• LogD (pH = 7.4): 2.0976188
• Log P: 2.1299
• Molar Refractivity: 47.3774 cm^3
• Polarizability: 19.811594 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 128-129°C; 135 °C (dec.)(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%; 98%
• Linear Formula: C2H5OCOC6H4B(OH)2

DETAILS

Sigma Aldrich - 574643

Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Oxidative hydroxylation for the preparation of phenols1
• Homolytic aromatic substitution2
• Cross-coupling with α-bromocarbonyl compounds3
• Suzuki-coupling reaction with quinoline carboxylates4
• Trifluoromethylation5
• Carbometalation of ynamides6