4-nitro-1H-indole

• ChemBase ID: 12050
• Molecular Formular: C8H6N2O2
• Molecular Mass: 162.14544
• Monoisotopic Mass: 162.04292744
• SMILES: c1c[nH]c2c1c(ccc2)[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1cccc2c1cc[nH]2
• InChI: InChI=1S/C8H6N2O2/c11-10(12)8-3-1-2-7-6(8)4-5-9-7/h1-5,9H
• InChIKey: LAVZKLJDKGRZJG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitro-1H-indole
• IUPAC Traditional name: 4-nitro-1H-indole
• Synonyms: 4-Nitroindole; 4-Nitro-1H-indole 97%; 4-Nitroindole; 4-nitro-1H-indole; 4-Nitro-1H-indole; 4-硝基吲哚

Database IDs

• CAS Number: 4769-97-5
• MDL Number: MFCD00010056
• Beilstein Number: 136022
• PubChem SID: 160975357; 24856183
• PubChem CID: 145766

CALCULATED PROPERTIES

• Acid pKa: 13.255104
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.011992
• LogD (pH = 7.4): 2.0119915
• Log P: 2.011992
• Molar Refractivity: 43.465 cm^3
• Polarizability: 17.394144 Å^3
• Polar Surface Area: 58.93 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Crystalline Solid
• Melting Point: 202-207°C; 205-207 °C(lit.); 205-207°C; 205-207°C; 206 - 207°C
• Hydrophobicity(logP): 2.235

Safety Information

• Storage Warning: Irritant; IRRITANT, IRRITANT-HARMFUL
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%; 98%
• Empirical Formula (Hill Notation): C8H6N2O2

DETAILS

Sigma Aldrich - 269964

Packaging
1 g in glass bottle
500 mg in glass bottle
Application
Reactant for preparation of:
• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1
• Meridianin derivatives as protein kinase (PKC) inhibitors and vitro antiproliferative agents2
• Anti-angiogenic agents3
• Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes4
• Biologically active indoles5
• CGRP receptor antagonists6
• Nucleosides7
• CB2 cannabinoid receptor ligands8

Toronto Research Chemicals - N496275

4-Nitroindole is an intermediate for the preparation of indole compounds useful in treatment of pain, inflammation.

REFERENCES

• Leclerc, S., et al.: J. Biol. Chem., 276, 251 (2001)
• Meijer, L., et al.: Chem. Biol., 10, 1255 (2001)
• Alonso, M., et al.: Curr. Med. Chem., 11, 755 (2001)