1H-indole-2-carboxylic acid

• ChemBase ID: 13653
• Molecular Formular: C9H7NO2
• Molecular Mass: 161.15738
• Monoisotopic Mass: 161.04767847
• SMILES: c1([nH]c2c(c1)cccc2)C(=O)O
• Canonical SMILES: OC(=O)c1cc2c([nH]1)cccc2
• InChI: InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
• InChIKey: HCUARRIEZVDMPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole-2-carboxylic acid
• IUPAC Traditional name: indole-2-carboxylic acid
• Synonyms: 2-Indolylformic acid; NSC 16598; Indole-2-carboxylic acid; 1H-Indole-2-carboxylic acid; Indole-2-carboxylic acid; 2-Carboxyindole; N-p-Chlorobenzyl-N',N'-dimethyl-N-[2-pyridyl]lethylenediamine; CHLOROPYRAMINE; INDOLE-2-CARBOXLIC ACID; 2-羧基吲哚; 吲哚-2-羧酸

Database IDs

• CAS Number: 1477-50-5; 6170-42-9
• EC Number: 216-030-4; 228-216-2
• MDL Number: MFCD00005611
• Beilstein Number: 124132
• PubChem SID: 160976960; 24895981
• PubChem CID: 72899

CALCULATED PROPERTIES

• Acid pKa: 3.5999553
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.24580903
• LogD (pH = 7.4): -1.693461
• Log P: 1.6495918
• Molar Refractivity: 44.2782 cm^3
• Polarizability: 17.864708 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Clear Yellow Solution 5% in Ethanol
• Apperance: Yellow Crystalline Powder
• Melting Point: 172-174; 202-206 °C(lit.); 203-206°C; 204-206°C; 204-209 °C; 205-208°C; ca 205°C dec.

Safety Information

• Storage Condition: 2-8°C; Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Irritant
• RTECS: NK7882812
• European Hazard Symbols: X
• German water hazard class: 3
• Risk Statements: 21/22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06
• GHS Hazard statements: H301-H311-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... SRD5A1(6715)rat ... Grin2a(24409)

Product Information

• Purity: ~99%; ≥98.0% (T); 97%; 98%; 98+%
• Grade: purum
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C9H7NO2
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05204705

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151321

Crystalline
Purity: ~99%

MP Biomedicals - 02154974

(N-p-Chlorobenzyl-N',N'-dimethyl- N-[2-pyridyl]lethylenediamine) Hydrochloride

Sigma Aldrich - 57220

Application

• Reactant for total synthesis of (±)-dibromophakellin and analogs1
• Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine2
• Reactant for stereoselective preparation of renieramycin G analogs3
• Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization4
• Reactant for Pd-catalyzed cyclization5
• Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives6

Sigma Aldrich - I5109

Packaging
10, 50 g in poly bottle
5 g in glass bottle
Application

• Reactant for total synthesis of (±)-dibromophakellin and analogs1
• Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine2
• Reactant for stereoselective preparation of renieramycin G analogs3
• Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization4
• Reactant for Pd-catalyzed cyclization5
• Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives6