16-nitro-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-amine

• ChemBase ID: 148601
• Molecular Formular: C14H20N2O7
• Molecular Mass: 328.3178
• Monoisotopic Mass: 328.12705099
• SMILES: c1c(c(cc2c1OCCOCCOCCOCCO2)[N+](=O)[O-])N
• Canonical SMILES: [O-][N+](=O)c1cc2OCCOCCOCCOCCOc2cc1N
• InChI: InChI=1S/C14H20N2O7/c15-11-9-13-14(10-12(11)16(17)18)23-8-6-21-4-2-19-1-3-20-5-7-22-13/h9-10H,1-8,15H2
• InChIKey: PSFJQUGCUJJHIS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16-nitro-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-amine
• IUPAC Traditional name: 16-nitro-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-amine
• Synonyms: 4′-Amino-5′-nitrobenzo-15-crown-5; 4′-氨基-5′-硝基苯并-15-冠-5

Database IDs

• CAS Number: 77001-50-4
• MDL Number: MFCD00188437
• Beilstein Number: 5298835
• PubChem SID: 24846225; 162242776; 24868096
• PubChem CID: 5098453

CALCULATED PROPERTIES

• Acid pKa: 16.202776
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.106508
• LogD (pH = 7.4): 1.10651
• Log P: 1.10651
• Molar Refractivity: 82.171 cm^3
• Polarizability: 30.946077 Å^3
• Polar Surface Area: 117.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 148-151 °C(lit.); 148-152 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• 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

Product Information

• Purity: ≥97.0% (CHN); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C14H20N2O7

DETAILS

Sigma Aldrich - 444030

Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 08840

Other Notes
Versatile starting material for the synthesis of modified crowns1,2,3