2-(5-bromothiophen-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

• ChemBase ID: 141660
• Molecular Formular: C9H9BBrNO4S
• Molecular Mass: 317.95206
• Monoisotopic Mass: 316.95287117
• SMILES: B1(OC(=O)CN(CC(=O)O1)C)c1ccc(s1)Br
• Canonical SMILES: CN1CC(=O)OB(OC(=O)C1)c1ccc(s1)Br
• InChI: InChI=1S/C9H9BBrNO4S/c1-12-4-8(13)15-10(16-9(14)5-12)6-2-3-7(11)17-6/h2-3H,4-5H2,1H3
• InChIKey: IHKDTCFWTZPRTA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-bromothiophen-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• IUPAC Traditional name: 2-(5-bromothiophen-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• Synonyms: 2-(5-Bromothiophen-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione; 5-Bromothiophene-2-boronic acid MIDA ester; 5-Bromo-2-thiophenylboronic acid MIDA ester; 2-(5-溴噻吩-2-基)-6-甲基-1,3,6,2-二氧氮杂硼烷-4,8-二酮; 5-溴噻吩-2-硼酸甲基亚氨基二乙酸酯; 5-溴-2-苯硫基硼酸甲基亚氨基二乙酸酯

Database IDs

• CAS Number: 943552-31-6
• MDL Number: MFCD11215240
• PubChem SID: 162235894
• PubChem CID: 50896239

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.4836226
• LogD (pH = 7.4): 2.4852788
• Log P: 2.4853
• Molar Refractivity: 58.8248 cm^3
• Polarizability: 25.607117 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 151-156 °C

Safety Information

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

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C9H9BBrNO4S

DETAILS

Sigma Aldrich - 701092

Packaging
1, 5 g in glass bottle
Application
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings1,2Suzuki Cross-Coupling with MIDA Boronates