6-amino-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

• ChemBase ID: 7792
• Molecular Formular: C8H6N2O3
• Molecular Mass: 178.14484
• Monoisotopic Mass: 178.03784206
• SMILES: c1(ccc2c(c1)c(=O)oc(=O)[nH]2)N
• Canonical SMILES: Nc1ccc2c(c1)c(=O)oc(=O)[nH]2
• InChI: InChI=1S/C8H6N2O3/c9-4-1-2-6-5(3-4)7(11)13-8(12)10-6/h1-3H,9H2,(H,10,12)
• InChIKey: QEQDLBKVHJXPJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
• IUPAC Traditional name: 6-amino-1H-3,1-benzoxazine-2,4-dione
• Synonyms: 5-Aminoisatoic anhydride, tech.; 5-Aminoisatoic anhydride; 5-氨基靛红酸酐

Database IDs

• CAS Number: 169037-24-5; 205688-52-4
• MDL Number: MFCD00060534
• PubChem SID: 24879860; 160971099
• PubChem CID: 2735353

CALCULATED PROPERTIES

• Acid pKa: 9.759998
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.6469035
• LogD (pH = 7.4): 0.6453818
• Log P: 0.6471822
• Molar Refractivity: 46.5267 cm^3
• Polarizability: 16.443466 Å^3
• Polar Surface Area: 81.42 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); 230°C(dec); 230(dec.)°C

Safety Information

• Storage Warning: IRRITANT; Toxic/Irritant/Corrosive/Air Sensitive/Moisture Sensitive/Store under Argon
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38-43
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H317-H318-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Impurities: ≤10% DMF, may contain
• Empirical Formula (Hill Notation): C8H6N2O3

DETAILS

Sigma Aldrich - 560278

Packaging
1 g in glass bottle
Application
Reactant for:
• β-cyclodextrin catalyzed synthesis of tryptanthrin and its analogs in water1
• Synthesis of amino-chloroquinolyl derivatives as antimalarial agents2