(4R,5R)-2-(3-nitrophenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid

• ChemBase ID: 140681
• Molecular Formular: C10H8BNO8
• Molecular Mass: 280.98342
• Monoisotopic Mass: 281.03429662
• SMILES: B1(O[C@H]([C@@H](O1)C(=O)O)C(=O)O)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: OC(=O)[C@@H]1OB(O[C@H]1C(=O)O)c1cccc(c1)[N+](=O)[O-]
• InChI: InChI=1S/C10H8BNO8/c13-9(14)7-8(10(15)16)20-11(19-7)5-2-1-3-6(4-5)12(17)18/h1-4,7-8H,(H,13,14)(H,15,16)/t7-,8-/m1/s1
• InChIKey: DKYPDMHYDHHGRL-HTQZYQBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5R)-2-(3-nitrophenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid
• IUPAC Traditional name: (4R,5R)-2-(3-nitrophenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid
• Synonyms: L-TarB-NO2; 2-(3-Nitrophenyl)-1,3,2-dioxaborolane-4R,5R-dicarboxylic acid; 3-Nitrophenylboronic acid L-tartaric acid ester solution; 2-(3-硝基苯基)-1,3,2-二氧杂戊硼烷-4R,5R-二甲酸; 3-硝基苯硼酸 L-酒石酸酯

Database IDs

• CAS Number: 467443-01-2
• MDL Number: MFCD09750458
• PubChem SID: 162234922; 24885731
• PubChem CID: 11460197

CALCULATED PROPERTIES

• Acid pKa: 2.0484643
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.3858678
• LogD (pH = 7.4): -4.5251913
• Log P: 2.345
• Molar Refractivity: 56.5836 cm^3
• Polarizability: 23.552969 Å^3
• Polar Surface Area: 138.88 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 0 °F
• Density: 1.0525 g/mL at 25 °C
• Refractive Index: n20/D 1.4508
• Optical Rotation: [α]22/D +9.0°, neat

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 2056
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-19-36/37
• Safety Statements: 26
• RID/ADR: UN 2056 3/PG 2

Product Information

• Concentration: 1.0 M in THF
• Empirical Formula (Hill Notation): C10H8BNO8

DETAILS

Sigma Aldrich - 682713

Application
In conjunction with NaBH4, this Lewis acid reduces prochiral alkyl aryl ketones with excellent enantioselectivity.1,2
Packaging
5, 25 mL in glass bottle