(1R,2S,6R,7S)-4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

• ChemBase ID: 151434
• Molecular Formular: C9H9NO3
• Molecular Mass: 179.17266
• Monoisotopic Mass: 179.05824315
• SMILES: C1[C@@H]2C=C[C@H]1[C@@H]1[C@H]2C(=O)N(C1=O)O
• Canonical SMILES: ON1C(=O)[C@@H]2[C@H](C1=O)[C@H]1C[C@@H]2C=C1
• InChI: InChI=1S/C9H9NO3/c11-8-6-4-1-2-5(3-4)7(6)9(12)10(8)13/h1-2,4-7,13H,3H2/t4-,5+,6-,7+
• InChIKey: ZUSSTQCWRDLYJA-UMRXKNAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,6R,7S)-4-hydroxy-4-azatricyclo[5.2.1.0^2,^6]dec-8-ene-3,5-dione
• IUPAC Traditional name: (1R,2S,6R,7S)-4-hydroxy-4-azatricyclo[5.2.1.0^2,^6]dec-8-ene-3,5-dione
• Synonyms: HONB; N-Hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide; N-Hydroxy-5-norbornene-2,3-dicarboxylic acid imide; N-羟基-5-降冰片烯-2,3-二甲酰亚胺; N-羟基-5-降冰片烯-2,3-二甲酰亚胺

Database IDs

• CAS Number: 21715-90-2
• EC Number: 244-538-6
• MDL Number: MFCD00065691
• Beilstein Number: 13540
• PubChem SID: 162245587; 24853563
• PubChem CID: 6541657

CALCULATED PROPERTIES

• Acid pKa: 7.1724677
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.1905442
• LogD (pH = 7.4): -0.6079052
• Log P: -0.18144734
• Molar Refractivity: 44.4054 cm^3
• Polarizability: 16.86843 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165-170 °C(lit.); 166-169 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: ≥96.0% (T); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C9H9NO3

DETAILS

Sigma Aldrich - 226378

Packaging
50 g in glass bottle

Sigma Aldrich - 56055

Other Notes
Excellent reagent to be used in combination with DCC for peptide synthesis; the reagent decreases racemization, inhibits formation of N-acylureas and affords peptides in high yields1,2; the corresponding chloroformate can be used for the introduction of various amino-protecting groups3