4-nitro-1,3-dihydro-2-benzofuran-1,3-dione

• ChemBase ID: 70008
• Molecular Formular: C8H3NO5
• Molecular Mass: 193.11312
• Monoisotopic Mass: 193.0011222
• SMILES: C1(=O)c2c(C(=O)O1)c(ccc2)[N+](=O)[O-]
• Canonical SMILES: O=C1OC(=O)c2c1cccc2[N+](=O)[O-]
• InChI: InChI=1S/C8H3NO5/c10-7-4-2-1-3-5(9(12)13)6(4)8(11)14-7/h1-3H
• InChIKey: ROFZMKDROVBLNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitro-1,3-dihydro-2-benzofuran-1,3-dione
• IUPAC Traditional name: 4-nitro-2-benzofuran-1,3-dione
• Synonyms: 3-Nitrophthalic anhydride; 4-Nitrobenzo[c]furan-1,3-dione; 4-Nitro-2-benzofuran-1,3-dione; 4-Nitroisobenzofuran-1,3-dione; 3-Nitrophthalic anhydride 98%; 3-Nitrophthalic anhydride; 4-Nitro-1,3-isobenzofurandione; 3-Nitrophthalic Acid Anhydride; NSC 27006; NSC 4134; 3-硝基邻苯二甲酸酐

Database IDs

• CAS Number: 641-70-3
• EC Number: 211-373-6
• MDL Number: MFCD00005921
• Beilstein Number: 179963
• PubChem SID: 24886606; 24849643; 162035733
• PubChem CID: 21631

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.3625678
• LogD (pH = 7.4): 1.3625678
• Log P: 1.3625678
• Molar Refractivity: 43.6855 cm^3
• Polarizability: 16.151567 Å^3
• Polar Surface Area: 86.51 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 161-166°C; 162-165 °C; 163-165 °C(lit.); 163-165°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Hygroscopic/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥96.0% (NT); 95+%; 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C8H3NO5

DETAILS

Sigma Aldrich - 156884

Packaging
5, 25 g in glass bottle
Application
Reactions with aminoquinazolinones yield phthalimidoquinazolinones.1

Toronto Research Chemicals - N515320

An intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472).

REFERENCES

• Denny, W., et al.: J. Med. Chem., 33, 814 (1990)
• Anon., et al.: Curr. Med. Chem., 10, 321 (1990)
• Has been used as an N-blocking group for amino acids in solid-phase peptide synthesis, providing an acidic 'handle' allowing separation by ion-exchange chromatography: Angew. Chem. Int. Ed., 8, 764 (1969). See Appendix 6.