(1-phenylethenyl)boronic acid

• ChemBase ID: 88845
• Molecular Formular: C8H9BO2
• Molecular Mass: 147.96686
• Monoisotopic Mass: 148.06955993
• SMILES: B(C(=C)c1ccccc1)(O)O
• Canonical SMILES: OB(C(=C)c1ccccc1)O
• InChI: InChI=1S/C8H9BO2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-6,10-11H,1H2
• InChIKey: YJCPVMYUISTDKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1-phenylethenyl)boronic acid
• IUPAC Traditional name: 1-phenylethenylboronic acid
• Synonyms: 1-Phenylvinylboronic acid 95%; 1-PHENYLVINYLBORONIC ACID; α-Methylene-α-tolueneboronic acid; (1-Phenylethenyl)boronic acid; Styrene α-boronic acid; α-Phenyl vinylboronic acid; 1-Phenylvinylboronic acid; α-苯基乙烯基硼酸; 1-苯基乙烯基硼酸

Database IDs

• CAS Number: 14900-39-1
• MDL Number: MFCD01074578
• PubChem SID: 24880629; 162075743
• PubChem CID: 5003684

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.5375714
• LogD (pH = 7.4): 1.5353332
• Log P: 1.5376
• Molar Refractivity: 40.2012 cm^3
• Polarizability: 17.073353 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 9.678851

PROPERTIES

Physical Property

• Melting Point: 125 °C (dec.)(lit.); 80-86°C

Safety Information

• Storage Warning: Irritant/Keep Cold
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 98%
• Linear Formula: C6H5C=CH2B(OH)2

DETAILS

Sigma Aldrich - 571350

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Halogenation of alkynes for preparation of enol esters1
• Liebeskind-Srogl cross-coupling2
• Homocoupling of arylboronic acids for synthesis of biaryls3
• Iterative cross-coupling of boronate building blocks4
• Enantioselective hydrogenation of hydroxyphenyl styrenes5
• Samarium diiodide-mediated cyclization for synthesis of substituted benzannulated cyclooctanol derivatives6
• Suzuki-Miyaura cross-coupling for synthesis of C-6-substituted uridine phosphonates7