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

• ChemBase ID: 70750
• Molecular Formular: C13H19BO3
• Molecular Mass: 234.09916
• Monoisotopic Mass: 234.14272487
• SMILES: O1B(OC(C1(C)C)(C)C)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C13H19BO3/c1-12(2)13(3,4)17-14(16-12)10-6-8-11(15-5)9-7-10/h6-9H,1-5H3
• InChIKey: VFIKPDSQDNROGM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• IUPAC Traditional name: 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4-Methoxybenzeneboronic acid, pinacol ester; 4-METHOXYPHENYLBORONIC ACID, PINACOL ESTER; 4,4,5,5-Tetramethyl-2-(4-methoxyphenyl)-1,3,2-dioxaborolane; 4-Methoxy-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene; p-(Pinacolboryl)anisol; 4-Methoxyphenylboronic Acid Pinacol Ester

Database IDs

• CAS Number: 171364-79-7
• MDL Number: MFCD05663864
• PubChem SID: 162036463
• PubChem CID: 584319

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.6477
• LogD (pH = 7.4): 3.6477
• Log P: 3.6477
• Molar Refractivity: 62.1763 cm^3
• Polarizability: 26.516508 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT; Irritant
• TSCA Listed: false

Product Information

• Purity: 95+%; 97%; 98%

DETAILS

Toronto Research Chemicals - M265910

4-Methoxyphenylboronic Acid Pinacol Ester is an arylboronate ester used in the copper-catalyzed alkylation and arylation of chiral propargylic phosphates as well as in Suzuki-Miyaura coupling reaction.

REFERENCES

• Uehling, M. et al.: Org. Lett., 14, 362 (2012)
• Ciayadi, R. et al.: Bioorg. Med. Chem. Lett., 21, 5642 (2012)