4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

• ChemBase ID: 103316
• Molecular Formular: C9H9NO3
• Molecular Mass: 179.17266
• Monoisotopic Mass: 179.05824315
• SMILES: ON1C(=O)C2C3CC(C=C3)C2C1=O
• Canonical SMILES: ON1C(=O)C2C(C1=O)C1CC2C=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
• InChIKey: ZUSSTQCWRDLYJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-4-azatricyclo[5.2.1.0^2,^6]dec-8-ene-3,5-dione; 4-hydroxy-4-azatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione
• IUPAC Traditional name: 4-hydroxy-4-azatricyclo[5.2.1.0^2,^6]dec-8-ene-3,5-dione; 4-hydroxy-4-azatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione
• Synonyms: 2-Hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione; HONB; N-Hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide; N-HYDROXY-5-NORBORNENE-2,3-DICARBOXIMIDE; endo-N-Hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboximide; endo-N-Hydroxy-5-norbornene-2,3-dicarboximide; 内-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: 162090662
• PubChem CID: 89529

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: 166-170°C

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 95+%; 97%

DETAILS

MP Biomedicals - 02151302

Used with DCC in peptide synthesis to decrease racemization and increase yields.

REFERENCES

• Chem. Pharm. Bull., 22: 1857, (1974).
• Reportedly superior to N-Hydroxysuccinimide, A10312 as a racemization suppressant in peptide synthesis: Chem. Pharm. Bull., 22, 1857 (1974); 26, 585 (1978). See Appendix 6.
• Reagent for preparation of O-alkylhydroxylamines by O-alkylation and cleavage with hydrazine: Bull. Soc. Chim. Fr., 833 (1976). Compare N-Hydroxyphthalimide, A13862.