2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

• ChemBase ID: 75172
• Molecular Formular: C12H17BO3
• Molecular Mass: 220.07258
• Monoisotopic Mass: 220.1270748
• SMILES: Oc1ccccc1B1OC(C(O1)(C)C)(C)C
• Canonical SMILES: Oc1ccccc1B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C12H17BO3/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8,14H,1-4H3
• InChIKey: VLROJECCXBBKPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• IUPAC Traditional name: 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• Synonyms: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; 2-(2-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-Hydroxybenzeneboronic acid, pinacol ester; 2-Hydroxyphenylboronic acid pinacol ester; 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL; 2-(4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷-2-基)苯酚; 2-羟基苯硼酸频哪醇酯

Database IDs

• CAS Number: 269409-97-4
• MDL Number: MFCD02093754
• PubChem SID: 24874280; 162040090
• PubChem CID: 2734622

CALCULATED PROPERTIES

• Acid pKa: 8.407679
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6154647
• LogD (pH = 7.4): 3.575411
• Log P: 3.616
• Molar Refractivity: 57.694 cm^3
• Polarizability: 24.6035 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 282 °C(lit.); 282°C
• Flash Point: >110 °C; >230 °F
• Density: 1.05; 1.05 g/mL at 25 °C(lit.)
• Refractive Index: 1.506; n20/D 1.506(lit.)

Safety Information

• Storage Warning: Harmful/Irritant/Moisture Sensitive/Store under Argon
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C12H17BO3

DETAILS

Sigma Aldrich - 522554

Application
Widely used in Suzuki coupling chemistry.6
Reactant involved in:
• Synthesis of indolo-fused heterocyclic inhibitors of polymerase enzyme of hepatitis C1
• Studies of pi-interactions, electronic structure and transient UV absorption of subphthalocyanine-borate-bridged ferrocene-fullerene conjugates2
• Synthesis of subphthalocyanine3 and fused-ring nicotine derivatives4
• Suzuki-Miyaura coupling-triflation sequence, reduction and salt formation for synthesis of hydroxylated oligoarene phosphines5
Packaging
1, 5 g in glass bottle