(2-phenylethenyl)boronic acid

• ChemBase ID: 74813
• 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/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7,10-11H
• InChIKey: VKIJXFIYBAYHOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-phenylethenyl)boronic acid; [(E)-2-phenylethenyl]boronic acid
• IUPAC Traditional name: 2-phenylethenylboronic acid; (E)-2-phenylethenylboronic acid
• Synonyms: (E)-Phenylethenylboronic acid; trans-Phenylethenylboronic acid; TRANS-2-PHENYLVINYLBORONIC ACID; (E)-Styrylboronic acid; (E)-2-phenyl-Etheneboronic acid; (E)-Phenylethenylboronic acid; (E)-Styreneboronic acid; (E)-Styrylboronic acid; trans-(2-Phenylethenyl)boronic acid; trans-Phenylvinyl boronic acid; trans-2-Phenylvinylboronic acid; 反式-2-苯基乙烯基硼酸

Database IDs

• CAS Number: 6783-05-7; 4363-35-3
• MDL Number: MFCD00963621
• PubChem SID: 162039731; 24870932
• PubChem CID: 5702628

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.3751793
• LogD (pH = 7.4): 2.3735633
• Log P: 2.3752
• Molar Refractivity: 40.38 cm^3
• Polarizability: 17.077312 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 9.820617

PROPERTIES

Physical Property

• Melting Point: 146-156 °C(lit.); 146-156°C; 163-164°C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 98%
• Linear Formula: C6H5CH=CHB(OH)2

DETAILS

Sigma Aldrich - 473790

Other Notes
Contains varying amounts of anhydride
Packaging
25 g in poly bottle
5 g in glass bottle
Application
Reagent used for
• Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions1
• Rhodium (Rh)-catalyzed intramolecular amination of aryl azides2
• Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction3
• Copper (Cu)-mediated cyanation4
• Rhodium (Rh)-catalyzed asymmetric addition5
• Diastereoselective synthesis via iridium (Ir)-catalyzed addition6
• Palladium (Pd)-catalyzed cascade cyclization7 Reagent used in Preparation of
• Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction8
• Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization9