[(E)-2-(3-fluorophenyl)ethenyl]boronic acid

• ChemBase ID: 142226
• Molecular Formular: C8H8BFO2
• Molecular Mass: 165.9573232
• Monoisotopic Mass: 166.06013812
• SMILES: B(/C=C/c1cccc(c1)F)(O)O
• Canonical SMILES: OB(/C=C/c1cccc(c1)F)O
• InChI: InChI=1S/C8H8BFO2/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,11-12H/b5-4+
• InChIKey: ONXKUGHKGCSZJO-SNAWJCMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(E)-2-(3-fluorophenyl)ethenyl]boronic acid
• IUPAC Traditional name: (E)-2-(3-fluorophenyl)ethenylboronic acid
• Synonyms: TRANS-2-(3-FLUOROPHENYL)VINYLBORONIC ACID; (E)-2-(3-Fluorophenyl)ethenylboronic acid; trans-2-(3-Fluorophenyl)vinylboronic acid; 反式-2-(3-氟苯基)乙烯基硼酸

Database IDs

• CAS Number: 849062-22-2
• MDL Number: MFCD06008297
• PubChem SID: 162236456; 24882901
• PubChem CID: 16217749

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.5146794
• LogD (pH = 7.4): 2.5130613
• Log P: 2.5147
• Molar Refractivity: 40.5964 cm^3
• Polarizability: 16.72874 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 9.820095

PROPERTIES

Physical Property

• Melting Point: 184-186 °C(lit.)

Safety Information

• German water hazard class: 3

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C8H8FBO2

DETAILS

Sigma Aldrich - 637971

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Enantioselective diastereoselective synthesis of tetracyclins via metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation and Friedel-Crafts alkylation1
• Palladium-catalyzed Suzuki-Miyaura coupling reactions2
• Preparation of anticonvulsant agents3
• Preparation of piperazinyl pyrimidylhydroxamic acid deriatives as histone deacetylase inhibitors and antitumor agents4
• Preparation of ethyl-substituted conjugated dienoates and dienones by stereoselective Suzuki cross-coupling5