(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

• ChemBase ID: 69898
• Molecular Formular: C9H12N2O4
• Molecular Mass: 212.20258
• Monoisotopic Mass: 212.07970687
• SMILES: [C@H]([C@H](CO)N)(O)c1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: OC[C@@H]([C@H](c1ccc(cc1)[N+](=O)[O-])O)N
• InChI: InChI=1S/C9H12N2O4/c10-8(5-12)9(13)6-1-3-7(4-2-6)11(14)15/h1-4,8-9,12-13H,5,10H2/t8-,9-/m0/s1
• InChIKey: OCYJXSUPZMNXEN-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
• IUPAC Traditional name: (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
• Synonyms: (1S,2S)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; (2S,3S)-2-Amino-3-(4-nitrophenyl)propane-1,3-diol; Dextramine; L-(+)-threo-1-(p-Nitrophenyl)-2-amino-1,3-propanediol; L-(p-Nitrophenyl)-2-amino-1,3-propanediol; L-1-(p-Nitrophenyl)-2-aminopropane-1,3-diol; NSC 12466; Threomine; threo-(1S,2S)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; L-threo-(+)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; (1S,2S)-(+)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; (1S,2S)-(+)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; L-(+)-苏-2-氨基-1-(4-硝基苯基)-1,3-丙二醇; (1S,2S)-(+)-2-氨基-1-(4-硝基苯基)-1,3-丙二醇

Database IDs

• CAS Number: 2964-48-9
• EC Number: 221-001-4
• MDL Number: MFCD00066778; MFCD00007359
• PubChem SID: 24870752; 162035623
• PubChem CID: 224171

CALCULATED PROPERTIES

• Acid pKa: 13.587292
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.0474396
• LogD (pH = 7.4): -1.5777653
• Log P: -0.22167145
• Molar Refractivity: 52.7769 cm^3
• Polarizability: 20.542435 Å^3
• Polar Surface Area: 109.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 163-166 °C(lit.)
• Optical Rotation: [α]23/D +31°, c = 1 in 6 M HCl

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95+%; 99%
• Linear Formula: O2NC6H4CH(OH)CH(NH2)CH2OH

DETAILS

Sigma Aldrich - 471674

Packaging
10, 50 g in glass bottle

Toronto Research Chemicals - A622685

Used in the synthesis of (4S,5S)-(-)-isocytoxazone.

REFERENCES

• Kakeya, H., et al.: J. Antibiot., 51, 1126 (1998)
• Carter, P., et al.: Bioorg. Med. Chem. Lett., 13, 1237 (1998)