(3-ethenylphenyl)boronic acid

• ChemBase ID: 91518
• Molecular Formular: C8H9BO2
• Molecular Mass: 147.96686
• Monoisotopic Mass: 148.06955993
• SMILES: B(c1cccc(c1)C=C)(O)O
• Canonical SMILES: C=Cc1cccc(c1)B(O)O
• InChI: InChI=1S/C8H9BO2/c1-2-7-4-3-5-8(6-7)9(10)11/h2-6,10-11H,1H2
• InChIKey: SYBQEKBVWDPVJM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-ethenylphenyl)boronic acid
• IUPAC Traditional name: 3-ethenylphenylboronic acid
• Synonyms: 3-Vinylbenzeneboronic acid; (3-Ethenylphenyl)boronic acid; m-Vinylbenzeneboronic acid; 3-Vinylphenylboronic acid; 3-VINYLPHENYLBORONIC ACID; Styrene-3-boronic acid; 3-Vinylphenylboronic acid; 3-Vinylbenzeneboronic acid; 3-乙烯基苯硼酸

Database IDs

• CAS Number: 15016-43-0
• EC Number: 000-000-0
• MDL Number: MFCD01074679
• Beilstein Number: 3030426
• PubChem SID: 162078217; 24885576
• PubChem CID: 4366886

CALCULATED PROPERTIES

• Acid pKa: 8.731008
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.5360463
• LogD (pH = 7.4): 2.516598
• Log P: 2.5363
• Molar Refractivity: 40.2898 cm^3
• Polarizability: 17.057842 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 127-129°C; 141-147 °C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22; 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C8H9BO2

DETAILS

Sigma Aldrich - 680575

General description
May contain varying amounts of anhydride.
Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura reactions1
• Molecular imprinting of fructose and pinacol2
• Synthesis of arylmercapturic acids via Chen-Lam-Evans arylation3
• Three-component cross-coupling yeilding diarylketones4
• Generation of acyl anion equivalents5