{4-[(tert-butyldimethylsilyl)oxy]phenyl}boronic acid

• ChemBase ID: 78729
• Molecular Formular: C12H21BO3Si
• Molecular Mass: 252.18984
• Monoisotopic Mass: 252.13530146
• SMILES: B(c1ccc(cc1)O[Si](C)(C)C(C)(C)C)(O)O
• Canonical SMILES: OB(c1ccc(cc1)O[Si](C(C)(C)C)(C)C)O
• InChI: InChI=1S/C12H21BO3Si/c1-12(2,3)17(4,5)16-11-8-6-10(7-9-11)13(14)15/h6-9,14-15H,1-5H3
• InChIKey: NVHHEADQQACSCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[(tert-butyldimethylsilyl)oxy]phenyl}boronic acid
• IUPAC Traditional name: 4-[(tert-butyldimethylsilyl)oxy]phenylboronic acid
• Synonyms: 4-(tert-Butyldimethylsilyloxy)benzeneboronic acid; 4-(tert-Butyldimethylsilyloxy)benzeneboronic acid; 4-(tert-Butyldimethylsilyloxy)phenylboronic acid; 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENYLBORONIC ACID; 4-(叔丁基二甲基硅氧基)苯基硼酸

Database IDs

• CAS Number: 159191-56-7
• MDL Number: MFCD03093888
• PubChem SID: 24874387; 162043492
• PubChem CID: 11107815

CALCULATED PROPERTIES

• Acid pKa: 8.899544
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.572928
• LogD (pH = 7.4): 3.559638
• Log P: 3.5731
• Molar Refractivity: 62.4325 cm^3
• Polarizability: 28.191282 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 194-198 °C(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95%; 98%
• Linear Formula: (CH3)3CSi(CH3)2OC6H4B(OH)2

DETAILS

Sigma Aldrich - 524042

Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Asymmetric addition reactions with β-substituted cyclic enones1
• Hydroarylation and heterocyclization with phenylpropiolates2
• Double Suzuki-Miyaura coupling reactions3Starting material for the synthesis of red electroluminescent polyfluorenes4Reactant involved in the synthesis of biologically active molecules including:
• Phenylpyridone derivatives as MCH1R antagonists5
• Atromentin and its O-alkylated derivatives3
• Gelatinases and MT1-MMP inhibitors6