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| | Indole-2-carboxylic acid Basic information |
| | Indole-2-carboxylic acid Chemical Properties |
| Melting point | 202-206 °C(lit.) | | Boiling point | 287.44°C (rough estimate) | | density | 1.2480 (rough estimate) | | refractive index | 1.5050 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in clear yellow solution 5% in ethanol, dimethyl sulfoxide and methanol. | | pka | 4.44±0.30(Predicted) | | form | Crystalline Powder or Crystals | | color | Off-white to yellow to brown | | BRN | 124132 | | 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 | | SMILES | N1C2=C(C=CC=C2)C=C1C(O)=O | | CAS DataBase Reference | 1477-50-5(CAS DataBase Reference) | | NIST Chemistry Reference | Indole-2-carboxylic acid(1477-50-5) |
| Hazard Codes | Xn,Xi | | Risk Statements | 36/37/38-21/22 | | Safety Statements | 22-24/25 | | WGK Germany | 3 | | RTECS | NK7882812 | | HazardClass | IRRITANT | | HS Code | 29339990 | | Storage Class | 11 - Combustible Solids |
| | Indole-2-carboxylic acid Usage And Synthesis |
| Chemical Properties | Yellow Crystalline Powder | | Uses | • ;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( | | Uses | Reactant for total synthesis of (±)-dibromophakellin and analogs, synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine, stereo selective preparation of renieramycin G analogs, preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization, Pd-catalyzed cyclization and N,N-(pentane)diylbis[indolecarboxamide] and N,N-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives. | | Definition | ChEBI: Indole-2-carboxylic acid is an indolyl carboxylic acid. | | Synthesis Reference(s) | Tetrahedron Letters, 33, p. 7961, 1992 DOI: 10.1016/S0040-4039(00)74789-7 | | Synthesis | Indole-2-carboxylic acid is prepared by a two-step condensation–reductive cyclization route: starting from 1-methyl-2-nitrobenzene (1) and diethyl oxalate (2), the intermediate sodium salt of 3-(2-nitrophenyl)-2-oxopropanoic acid (3) is first obtained by condensation, which is then reduced and cyclized to give the target product indole-2-carboxylic acid (4) [1].
 | | IC 50 | NMDA Receptor; Human Endogenous Metabolite | | References | [1]
Jiang, T., Liu, N., Jiang, Y.-W., Ye, P.-P., Xu, W.-M. (2017). A Practical Synthesis of Indole-2-carboxylic Acid. Organic Preparations and Procedures International, 49(5), 476–478. https://doi.org/10.1080/00304948.2017.1374138 |
| | Indole-2-carboxylic acid Preparation Products And Raw materials |
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