5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol

• ChemBase ID: 90392
• Molecular Formular: C11H16BNO3
• Molecular Mass: 221.06064
• Monoisotopic Mass: 221.12232378
• SMILES: O1C(C(C)(C)OB1c1ccc(nc1)O)(C)C
• Canonical SMILES: Oc1ccc(cn1)B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C11H16BNO3/c1-10(2)11(3,4)16-12(15-10)8-5-6-9(14)13-7-8/h5-7H,1-4H3,(H,13,14)
• InChIKey: WAUWXCUPDOXYKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol
• IUPAC Traditional name: 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol
• Synonyms: 6-Hydroxypyridine-3-boronic acid, pinacol ester; 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol; 2-Hydroxypyridine-5-boronic acid, pinacol ester; 2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine; 2-Hydroxypyridine-5-boronic acid, pinacol ester; 6-Hydroxypyridine-3-boronic acid pinacol ester; 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2(1H)-pyridinone; 6-Hydroxypyridine-3-boronic Acid Pinacol Ester; 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol; 2-羟基-5-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)吡啶; 2-羟基吡啶-5-硼酸频那醇酯; 6-羟基吡啶-3-硼酸频那醇酯; 2-羟基吡啶-5-硼酸频哪醇酯

Database IDs

• CAS Number: 1054483-78-1
• MDL Number: MFCD06795671
• PubChem SID: 162077205
• PubChem CID: 17750253

CALCULATED PROPERTIES

• Acid pKa: 10.429755
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.0026748
• LogD (pH = 7.4): 3.0023131
• Log P: 3.0027
• Molar Refractivity: 55.8506 cm^3
• Polarizability: 23.713045 Å^3
• Polar Surface Area: 51.58 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 196-200 °C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36-38
• Safety Statements: 26
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C11H16BNO3

DETAILS

Sigma Aldrich - 706094

Packaging
1 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - H953180

6-Hydroxypyridine-3-boronic Acid Pinacol ester is used in the preparation of modified C3 Betulinic acid (B330250) derivatives as HIV maturation inhibitors.

REFERENCES

• Zhu, Y., et al.: Bioorg. Med. Chem. Lett., 11, 3115 (2001)
• Ma, C., et al.: Chem. Pharm. Bull., 48, 1681 (2001)