(2R,3R,4S,5S,6R)-2-(2-chloro-4-nitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 164479
• Molecular Formular: C12H14ClNO8
• Molecular Mass: 335.69446
• Monoisotopic Mass: 335.04079409
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccc(cc1Cl)[N+](=O)[O-])O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2Cl)[N+](=O)[O-])[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H14ClNO8/c13-6-3-5(14(19)20)1-2-7(6)21-12-11(18)10(17)9(16)8(4-15)22-12/h1-3,8-12,15-18H,4H2/t8-,9-,10+,11-,12+/m1/s1
• InChIKey: PJCVBKZRKNFZOD-ZIQFBCGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-(2-chloro-4-nitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5S,6R)-2-(2-chloro-4-nitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 2-Chloro-4-nitrophenyl-α-D-glucopyranoside

Database IDs

• CAS Number: 119047-14-2
• PubChem SID: 162258614
• PubChem CID: 14457457

CALCULATED PROPERTIES

• Acid pKa: 12.200072
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.05435882
• LogD (pH = 7.4): -0.05436561
• Log P: -0.054358732
• Molar Refractivity: 72.3128 cm^3
• Polarizability: 28.651098 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 127-130°C

REFERENCES

• Montgomery, E.M. et al.: JACS, 64, 690-694 (1942)