[(E)-2-(4-methoxyphenyl)ethenyl]boronic acid

• ChemBase ID: 139398
• Molecular Formular: C9H11BO3
• Molecular Mass: 177.99284
• Monoisotopic Mass: 178.08012461
• SMILES: B(/C=C/c1ccc(cc1)OC)(O)O
• Canonical SMILES: COc1ccc(cc1)/C=C/B(O)O
• InChI: InChI=1S/C9H11BO3/c1-13-9-4-2-8(3-5-9)6-7-10(11)12/h2-7,11-12H,1H3/b7-6+
• InChIKey: LGSBCAPDUJYMOQ-VOTSOKGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(E)-2-(4-methoxyphenyl)ethenyl]boronic acid
• IUPAC Traditional name: (E)-2-(4-methoxyphenyl)ethenylboronic acid
• Synonyms: (E)-(4-Methoxystyryl)boronic acid; [(E)-2-(4-Methoxyphenyl)ethenyl]boronic acid; trans-2-(4-Methoxyphenyl)vinylboronic acid; TRANS-2-(4-METHOXYPHENYL)VINYLBORONIC ACID; 反-2-(4-甲氧基苯基)乙烯基硼酸

Database IDs

• CAS Number: 72316-18-8
• MDL Number: MFCD04039879
• PubChem SID: 24874057; 162233646
• PubChem CID: 642693

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.1224794
• LogD (pH = 7.4): 2.120864
• Log P: 2.1225
• Molar Refractivity: 46.8432 cm^3
• Polarizability: 19.58046 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 9.820804

PROPERTIES

Physical Property

• Melting Point: 140-144 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95%; 95+%; 98%
• Linear Formula: CH3OC6H4CH=CHB(OH)2

DETAILS

Sigma Aldrich - 518980

Other Notes
Contains varying amounts of anhydride
Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• Enantioselective conjugate addition reactions with indole-appended enones1
• Liebeskind-Srogl cross-coupling reactions2
• Petasis asymmetric dihydroxylation for synthesis of (dihydroxy)homotyrosines3
• Copper-catalyzed trifluoromethylation4
• Asymmetric Michael addition with hydroxycinnamaldehydes5
• Cobalt-catalyzed coupling for synthesis of phenylbutenylheteroarenes6