6-methyl-2-[1-(4-methylbenzenesulfonyl)-1H-pyrrol-2-yl]-1,3,6,2-dioxazaborocane-4,8-dione

• ChemBase ID: 143029
• Molecular Formular: C16H17BN2O6S
• Molecular Mass: 376.19198
• Monoisotopic Mass: 376.09003767
• SMILES: B1(OC(=O)CN(CC(=O)O1)C)c1cccn1S(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: CN1CC(=O)OB(OC(=O)C1)c1cccn1S(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C16H17BN2O6S/c1-12-5-7-13(8-6-12)26(22,23)19-9-3-4-14(19)17-24-15(20)10-18(2)11-16(21)25-17/h3-9H,10-11H2,1-2H3
• InChIKey: HLSJWIMKWDEIJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-methyl-2-[1-(4-methylbenzenesulfonyl)-1H-pyrrol-2-yl]-1,3,6,2-dioxazaborocane-4,8-dione
• IUPAC Traditional name: 6-methyl-2-[1-(4-methylbenzenesulfonyl)pyrrol-2-yl]-1,3,6,2-dioxazaborocane-4,8-dione
• Synonyms: 1-(p-Toluenesulfonyl)pyrrole-2-boronic acid MIDA ester; 1-(对甲苯磺酰基)吡咯-2-硼酸甲基亚氨基二乙酸酯

Database IDs

• CAS Number: 1311484-50-0
• MDL Number: MFCD15144862
• PubChem SID: 162237253
• PubChem CID: 71310855

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.8247924
• LogD (pH = 7.4): 2.8297367
• Log P: 2.8298
• Molar Refractivity: 87.85 cm^3
• Polarizability: 37.09593 Å^3
• Polar Surface Area: 94.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 216-220 °C

Safety Information

• German water hazard class: nwg

Product Information

• Empirical Formula (Hill Notation): C16H17BN2O6S

DETAILS

Sigma Aldrich - 717193

General description
Excludes solvent of crystallization. May contain up to 10 wt. % acetone.
Packaging
1, 5 g in glass bottle
Application
MIDA boronate involved in regioselective cross-coupling for synthesis of highly substituted biaryl scaffolds1Reactant for:Synthesis of atropisomerically defined, highly substituted biaryl scaffolds through catalytic enantioselective bromination and regioselective cross-coupling1MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings.Suzuki Cross-Coupling with MIDA Boronates