1H-indole-6-carboxylic acid

• ChemBase ID: 10059
• Molecular Formular: C9H7NO2
• Molecular Mass: 161.15738
• Monoisotopic Mass: 161.04767847
• SMILES: [nH]1ccc2c1cc(cc2)C(=O)O
• Canonical SMILES: OC(=O)c1ccc2c(c1)[nH]cc2
• InChI: InChI=1S/C9H7NO2/c11-9(12)7-2-1-6-3-4-10-8(6)5-7/h1-5,10H,(H,11,12)
• InChIKey: GHTDODSYDCPOCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole-6-carboxylic acid
• IUPAC Traditional name: 1H-indole-6-carboxylic acid
• Synonyms: Indole-6-carboxylic acid; 1H-Indole-6-carboxylic acid; 6-Carboxyindole; Indole-6-carboxylic acid; 吲哚-6-羧酸; 吲哚-6-甲酸

Database IDs

• CAS Number: 1670-81-1; 1670-82-2
• EC Number: 000-000-0
• MDL Number: MFCD00210441
• Beilstein Number: 123991
• PubChem SID: 24880873; 160973366
• PubChem CID: 595230

CALCULATED PROPERTIES

• Acid pKa: 3.6227784
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.14378846
• LogD (pH = 7.4): -1.6053637
• Log P: 1.7295908
• Molar Refractivity: 44.4007 cm^3
• Polarizability: 17.858837 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~255 °C; 249-253 °C(lit.); 249-253(dec.)°C; 256-259°C; 258 - 259°C; ca 258°C dec.
• Partition Coefficient: 1.989
• Hydrophobicity(logP): 2.067

Safety Information

• Storage Warning: Irritant/Light Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (T); 95%; 95+%; 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C9H7NO2

DETAILS

Sigma Aldrich - 576662

Packaging
5 g in glass bottle
Application

• Reactant for preparation of D-glutamic acid-based inhibitors of E. coli MurD ligase1
• Reactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitors2
• Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway3
• Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity4
• Reactant for preparation of pyridinyl carboxylates via esterification with chlorohydroxypyridine as SARS-CoV 3CL proinhibitors5
• Reactant for preparation of (indolecarbonyl)-D-phenylglycinamide amides as factor Xa inhibitors6

Sigma Aldrich - 57235

Caution
may discolor to deep yellow
Application

• Reactant for preparation of D-glutamic acid-based inhibitors of E. coli MurD ligase1
• Reactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitors2
• Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway3
• Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity4
• Reactant for preparation of pyridinyl carboxylates via esterification with chlorohydroxypyridine as SARS-CoV 3CL proinhibitors5
• Reactant for preparation of (indolecarbonyl)-D-phenylglycinamide amides as factor Xa inhibitors6