4-nitro-1H-indole-3-carbaldehyde

• ChemBase ID: 140967
• Molecular Formular: C9H6N2O3
• Molecular Mass: 190.15554
• Monoisotopic Mass: 190.03784206
• SMILES: c1cc2c(c(c1)[N+](=O)[O-])c(c[nH]2)C=O
• Canonical SMILES: O=Cc1c[nH]c2c1c(ccc2)[N+](=O)[O-]
• InChI: InChI=1S/C9H6N2O3/c12-5-6-4-10-7-2-1-3-8(9(6)7)11(13)14/h1-5,10H
• InChIKey: CGXVTWQTGQAMMX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitro-1H-indole-3-carbaldehyde
• IUPAC Traditional name: 4-nitro-1H-indole-3-carbaldehyde
• Synonyms: 3-Formyl-4-nitroindole; 4-Nitroindole-3-carboxaldehyde; 3-甲酰基-4-硝基吲哚; 4-硝基吲哚-3-甲醛

Database IDs

• CAS Number: 10553-11-4
• MDL Number: MFCD04973979
• PubChem SID: 162235204
• PubChem CID: 11095397

CALCULATED PROPERTIES

• Acid pKa: 11.283842
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.7244936
• LogD (pH = 7.4): 1.7244397
• Log P: 1.7244943
• Molar Refractivity: 51.0532 cm^3
• Polarizability: 19.30847 Å^3
• Polar Surface Area: 78.68 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 189-193 °C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C9H6N2O3

DETAILS

Sigma Aldrich - 691534

Packaging
1 g in glass bottle
Application

• reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators1
• reactant in synthesis of structural analogs of thaxtomin2
• reactant in preparation of chromophores related to gold fluorescent protein3
• reactant in preparation of brassinin and gramine derivatives4