4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane

• ChemBase ID: 141884
• Molecular Formular: C12H16BNO4
• Molecular Mass: 249.07074
• Monoisotopic Mass: 249.1172384
• SMILES: B1(OC(C(O1)(C)C)(C)C)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1cccc(c1)B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-6-5-7-10(8-9)14(15)16/h5-8H,1-4H3
• InChIKey: JWEAFTZTLIGAQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane
• IUPAC Traditional name: 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane
• Synonyms: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene; 4,4,5,5-Tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolan; 3-Nitrophenylboronic acid pinacol ester; 4,4,5,5-Tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane; 2-(3-Nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 3-Nitrobenzeneboronic Acid Pinacol Cyclic Ester; Pinacol 3-Nitrobenzeneboronate; 3-Nitrophenylboronic Acid Pinacol Ester; 3-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)硝基苯; 4,4,5,5-四甲基-2-(3-硝基苯基)-1,3,2-二氧杂戊硼烷; 3-硝基苯硼酸频哪醇酯

Database IDs

• CAS Number: 68716-48-3
• MDL Number: MFCD05663879
• PubChem SID: 24882506; 162236117
• PubChem CID: 11265164

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.854
• LogD (pH = 7.4): 3.854
• Log P: 3.854
• Molar Refractivity: 62.0336 cm^3
• Polarizability: 25.871016 Å^3
• Polar Surface Area: 61.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-80 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C12H16BNO4

DETAILS

Sigma Aldrich - 632708

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - N494320

3-Nitrophenylboronic Acid Pinacol Ester is used in the preparation of [(pyrimidoindolyl)phenyl]benzamide derivatives and analogs as Janus kinase inhibitors.

REFERENCES

• Hubschwerlen, C., et al.: J. Med, Chem., 35, 1385 (1992)