4,4,5,5-tetramethyl-2-(2-phenylethenyl)-1,3,2-dioxaborolane

• ChemBase ID: 75180
• Molecular Formular: C14H19BO2
• Molecular Mass: 230.11046
• Monoisotopic Mass: 230.14781025
• SMILES: B1(/C=C/c2ccccc2)OC(C(O1)(C)C)(C)C
• Canonical SMILES: CC1(C)OB(OC1(C)C)/C=C/c1ccccc1
• InChI: InChI=1S/C14H19BO2/c1-13(2)14(3,4)17-15(16-13)11-10-12-8-6-5-7-9-12/h5-11H,1-4H3
• InChIKey: ARAINKADEARZLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-2-(2-phenylethenyl)-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-[(E)-2-phenylethenyl]-1,3,2-dioxaborolane
• IUPAC Traditional name: 4,4,5,5-tetramethyl-2-(2-phenylethenyl)-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-[(E)-2-phenylethenyl]-1,3,2-dioxaborolane
• Synonyms: trans-beta-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene; (E)-2-Phenylethylene-1-boronic acid, pinacol ester; 4,4,5,5-Tetramethyl-2-((E)-2-phenylethenyl)-1,3,2-dioxaborolane; trans-2-Styreneboronic acid pinacol ester; trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene; trans-2-Phenylvinylboronic acid pinacol ester; (E)-4,4,5,5-Tetramethyl-2-(2-phenylvinyl)-1,3,2-dioxaborolane; (E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane; trans-beta-Styrylboronic acid pinacol ester; 反式-2-苯乙烯硼酸频哪醇酯; 反式-2-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)苯乙烯; 反式-2-苯基乙烯基硼酸频哪醇酯; 反式-beta-苯乙烯硼酸频哪酯

Database IDs

• CAS Number: 83947-56-2
• MDL Number: MFCD03453666
• Beilstein Number: 8617179
• PubChem SID: 162040098; 24880535
• PubChem CID: 5708413

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.6358
• LogD (pH = 7.4): 4.6358
• Log P: 4.6358
• Molar Refractivity: 65.4896 cm^3
• Polarizability: 27.56576 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 27-33 °C(lit.); 27-33°C; 27-33°C
• Boiling Point: 108-112°C; 128°C/4mm
• Flash Point: >110 °C; >110°C(230°F); >230 °F; 110°C
• Refractive Index: 1.5290

Safety Information

• Storage Warning: Irritant/Store under Argon/Moisture Sensitive
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 99%
• Linear Formula: C6H5CH=CHBO2C2(CH3)4

DETAILS

Sigma Aldrich - 570214

Packaging
1 g in glass bottle
Application
Reactant for:
• Oxidative coupling reactions catalyzed by areneruthenium1
• Cycloaddition reactions2
• Preparation of allyl vinyl ethers via Cu-catalyzed coupling with alcohols3
• Preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors4
• Diastereoselective addition to zincated hydrazones and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles5
• Regioselective and stereoselective Pd-catalyzed chelate-controlled intermolecular oxidative Heck reactions6