1H-indole-4-carboxylic acid

• ChemBase ID: 15060
• Molecular Formular: C9H7NO2
• Molecular Mass: 161.15738
• Monoisotopic Mass: 161.04767847
• SMILES: c1ccc2c(c1C(=O)O)cc[nH]2
• Canonical SMILES: OC(=O)c1cccc2c1cc[nH]2
• InChI: InChI=1S/C9H7NO2/c11-9(12)7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,(H,11,12)
• InChIKey: ROGHUJUFCRFUSO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole-4-carboxylic acid
• IUPAC Traditional name: 1H-indole-4-carboxylic acid
• Synonyms: 1H-4-indolecarboxylic acid; Indole-4-carboxylic acid; Indole-4-carboxylic acid; 4-Carboxyindole; 1H-Indole-4-carboxylic acid; 吲哚-4-羧酸

Database IDs

• CAS Number: 2142-55-2; 2124-55-2; 13544-43-9
• MDL Number: MFCD00009739
• PubChem SID: 24854799; 160978367
• PubChem CID: 595229

CALCULATED PROPERTIES

• Acid pKa: 3.5805833
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.18449251
• LogD (pH = 7.4): -1.6201264
• Log P: 1.7295908
• Molar Refractivity: 44.4007 cm^3
• Polarizability: 17.861128 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 213 - 214°C; 213-214 °C(lit.); 213-214°C
• Boiling Point: 213-214°C
• Hydrophobicity(logP): 2.067

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: false; 否
• 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: 90%; 95%; 97%; 98%
• Empirical Formula (Hill Notation): C9H7NO2

DETAILS

MP Biomedicals - 05203998

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 246263

Application
tert-butyl esters of indole and pyrrolecarboylic acids are readily prepared by direct treatment with N,N-dimethylformamide di-tert-butyl acetal (Cat. No. 395005).8

• Reactant for preparation of substituted indole derivatives as histamine H3 antagonists1
• Reactant for preparation of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-12
• Reactant for preparation of inhibitors of Gli1-mediated transcription in Hedgehog pathway3
• Reactant for preparation of pyridinyl carboxylates as SARS-CoV 3CL proinhibitors4
• Reactant for preparation of substituted bipiperidinylmethyl amides as CCR3 membrane binding ligands5
• Reactant for preparation of indole amide hydroxamic acids as potent inhibitors of histone deacetylases6
• Reactant for preparation of 2-[[[4′-chloro-[1,1-biphenyl]-4-yl]thio]methyl]-N-hydroxybutanamide derivatives as specific metalloproteinase7
Packaging
500 mg in glass bottle