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

• ChemBase ID: 141578
• Molecular Formular: C19H17BN2O6S
• Molecular Mass: 412.22408
• Monoisotopic Mass: 412.09003767
• SMILES: B1(OC(=O)CN(CC(=O)O1)C)c1cc2ccccc2n1S(=O)(=O)c1ccccc1
• Canonical SMILES: CN1CC(=O)OB(OC(=O)C1)c1cc2c(n1S(=O)(=O)c1ccccc1)cccc2
• InChI: InChI=1S/C19H17BN2O6S/c1-21-12-18(23)27-20(28-19(24)13-21)17-11-14-7-5-6-10-16(14)22(17)29(25,26)15-8-3-2-4-9-15/h2-11H,12-13H2,1H3
• InChIKey: MESWPWMZFWLPMN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-(benzenesulfonyl)-1H-indol-2-yl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• IUPAC Traditional name: 2-[1-(benzenesulfonyl)indol-2-yl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• Synonyms: 1-(Phenylsulfonyl)indole-2-boronic acid MIDA ester; 1-(Phenylsulfonyl)indole-2-boronic acid; Methyliminodiacetic acid anhydride; 1-(Phenylsulfonyl)-2-indolylboronic acid MIDA ester; 1-(Phenylsulfonyl)indole-3-boronic acid MIDA ester; 1-(Phenylsulfonyl)indole-3-boronic acid; 1-(Phenylsulfonyl)-3-indolylboronic acid MIDA ester; 1-(苯磺酰基)吲哚-2-硼酸; 1-(苯磺酰基)吲哚-2-硼酸甲基亚氨基二乙酸酯; 甲基亚氨基二乙酸酐; 1-苯磺酰基-2-吲哚基硼酸甲基亚氨基二乙酸酯

Database IDs

• CAS Number: 1158984-95-2
• MDL Number: MFCD11215206
• PubChem SID: 162235812
• PubChem CID: 44138340

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.4524698
• LogD (pH = 7.4): 3.4571402
• Log P: 3.4572
• Molar Refractivity: 99.1365 cm^3
• Polarizability: 42.77026 Å^3
• Polar Surface Area: 94.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 159-165 °C; 252-257 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C19H17BN2O6S

DETAILS

Sigma Aldrich - 697443

Application
Excludes solvent of crystallization. May contain up to 1.2 mole equivalence DMSO
MIDA boronate for slow-release cross-coupling1MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings.Suzuki Cross-Coupling with MIDA Boronates
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 732419

Packaging
1, 5 g in glass bottle
Legal Information
May be covered by one or more of US 2009/0030238 and WO 09/14550.