6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione

• ChemBase ID: 142868
• Molecular Formular: C10H11BN2O4
• Molecular Mass: 234.01634
• Monoisotopic Mass: 234.08118724
• SMILES: B1(OC(=O)CN(CC(=O)O1)C)c1ccccn1
• Canonical SMILES: CN1CC(=O)OB(OC(=O)C1)c1ccccn1
• InChI: InChI=1S/C10H11BN2O4/c1-13-6-9(14)16-11(17-10(15)7-13)8-4-2-3-5-12-8/h2-5H,6-7H2,1H3
• InChIKey: OEKJACZNFHBYNV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione
• IUPAC Traditional name: 6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione
• Synonyms: 2-Pyridinylboronic acid MIDA ester; 2-Pyridylboronic acid MIDA ester

Database IDs

• CAS Number: 1104637-58-2
• MDL Number: MFCD16621460
• PubChem SID: 162237094
• PubChem CID: 53378328

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.5577127
• LogD (pH = 7.4): 1.5617483
• Log P: 1.5618
• Molar Refractivity: 53.933 cm^3
• Polarizability: 22.986374 Å^3
• Polar Surface Area: 68.73 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Impurities: ≤15 wt. % DMSO
• Empirical Formula (Hill Notation): C10H11BN2O4

DETAILS

Sigma Aldrich - 719390

Application
2-Pyridinylboronic acid MIDA ester represents the first and only example of an air-stable 2-pyridinyl boronate.1 This stable boronic acid surrogate is a powerful cross coupling partner, useful in the synthesis of pharmaceuticals, natural products, and complex molecules.2
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings.Suzuki Cross-Coupling with MIDA Boronates
Packaging
1, 5, 25 g in glass bottle