5-nitro-1-benzofuran-2-carboxylic acid

• ChemBase ID: 8803
• Molecular Formular: C9H5NO5
• Molecular Mass: 207.1397
• Monoisotopic Mass: 207.01677227
• SMILES: c1(ccc2c(c1)cc(o2)C(=O)O)[N+](=O)[O-]
• Canonical SMILES: OC(=O)c1cc2c(o1)ccc(c2)[N+](=O)[O-]
• InChI: InChI=1S/C9H5NO5/c11-9(12)8-4-5-3-6(10(13)14)1-2-7(5)15-8/h1-4H,(H,11,12)
• InChIKey: LZKWLHXJPIKJSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-nitro-1-benzofuran-2-carboxylic acid
• IUPAC Traditional name: 5-nitro-1-benzofuran-2-carboxylic acid
• Synonyms: 5-Nitro-1-benzofuran-2-carboxylic acid; 5-Nitrobenzofuran-2-carboxylic acid; 2-Carboxy-5-nitrobenzofuran; 5-Nitro-2-benzofurancarboxylic acid; 5-Nitrobenzofuran-2-carboxylic acid; 5-硝基苯并呋喃-2-甲酸

Database IDs

• CAS Number: 10242-12-3
• MDL Number: MFCD00060513
• PubChem SID: 160972110
• PubChem CID: 1477128

CALCULATED PROPERTIES

• Acid pKa: 3.0920947
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.72802764
• LogD (pH = 7.4): -1.8126472
• Log P: 1.6499374
• Molar Refractivity: 48.3533 cm^3
• Polarizability: 19.00212 Å^3
• Polar Surface Area: 93.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 271 - 273°C; 274-275°C; 279-284 °C; 290 - 292 °C
• Hydrophobicity(logP): 2.345

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Purity: >95%; 95%; 97%; 98%
• Empirical Formula (Hill Notation): C9H5NO5

DETAILS

Sigma Aldrich - 716383

Packaging
1 g in glass bottle
Application
Reactant for:
• Preparation of arylarylamidobenzofurans via Curtius rearrangement followed by bromination and Suzuki reaction1
• Synthesis and antibacterial evaluation of nitazoxanide-based analogs2
• Preparation of Melanin-Concentrating Hormone Receptor 1 antagonist3
• Synthesis of benzoyl and cinnamoyl nitrogen mustard derivatives of benzoheterocyclic analogs of tallimustine as antitumor agents4