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

• ChemBase ID: 12420
• Molecular Formular: C12H16BNO4
• Molecular Mass: 249.07074
• Monoisotopic Mass: 249.1172384
• SMILES: c1c(ccc(c1)B1OC(C(O1)(C)C)(C)C)[N+](=O)[O-]
• Canonical SMILES: CC1(C)OB(OC1(C)C)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-5-7-10(8-6-9)14(15)16/h5-8H,1-4H3
• InChIKey: LUWACRUAJXZANC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 171364-83-3
• MDL Number: MFCD02179437
• PubChem SID: 24883300; 160975727
• PubChem CID: 2773555

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: 25.871689 Å^3
• Polar Surface Area: 61.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 108-109°C; 112-116 °C(lit.); 112-116°C

Safety Information

• Storage Warning: Harmful/Irritant/Hygroscopic/Air Sensitive/Keep Cold/Store under Argon; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Purity: 95%; 98%
• Empirical Formula (Hill Notation): C12H16BNO4

DETAILS

Sigma Aldrich - 643890

Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Synthesis of aryl azides 1
• Arylation of allylic chlorides2
• Syntehsis of RNA conjugates3
• Alkoxycarbonylation4
• Synthesis of mTOR and PI3K inhibitors as antitumor agents5
• Electrooxidative synthesis of biaryls6