methyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

• ChemBase ID: 75162
• Molecular Formular: C14H19BO4
• Molecular Mass: 262.10926
• Monoisotopic Mass: 262.13763949
• SMILES: O=C(c1cccc(c1)B1OC(C(O1)(C)C)(C)C)OC
• Canonical SMILES: COC(=O)c1cccc(c1)B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)11-8-6-7-10(9-11)12(16)17-5/h6-9H,1-5H3
• InChIKey: JBJGSVBGUBATNH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• IUPAC Traditional name: methyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• Synonyms: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic Acid Methyl Ester; 3-Methoxycarbonylphenylboronic Acid Pinacol Ester; Methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate; 3-(Methoxycarbonyl)benzeneboronic acid, pinacol ester; 3-Carbomethoxyphenylboronic acid pinacol ester; 3-Methoxycarbonylphenylboronic acid pinacol ester; 3-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)苯甲酸甲酯; 3-甲氧基羰基苯硼酸频哪醇酯; 3-甲氧羰基苯硼酸频哪醇酯

Database IDs

• CAS Number: 480425-35-2
• MDL Number: MFCD03789258
• PubChem SID: 162040080; 24881526
• PubChem CID: 2734651

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.048
• LogD (pH = 7.4): 4.048
• Log P: 4.048
• Molar Refractivity: 67.7384 cm^3
• Polarizability: 28.418022 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 91-95 °C(lit.); 91-95°C

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: 97%; 98%
• Empirical Formula (Hill Notation): C14H19BO4

DETAILS

Sigma Aldrich - 594652

Packaging
1 g in glass bottle

Toronto Research Chemicals - M226155

3-Methoxycarbonylphenylboronic Acid Pinacol Ester is used in the preparation of non-noviosylated coumermycin A1 analogs targeting heat shock protein 90 dimer with dimeric inhibitors.

REFERENCES

• Kusuma, B. et al.: J. Med. Chem., 54, 6234 (2011)