Identification | More | [Name]
Indol-1-yl-acetic acid | [CAS]
24297-59-4 | [Synonyms]
1H-INDOLE-1-ACETIC ACID ASINEX-REAG BAS 12457638 INDOL-1-YL-ACETIC ACID INDOLE-1-ACETIC ACID VITAS-BB TBB000210 2-(1H-Indol-1-yl)acetic acid 1H-indol-1-ylacetic acid | [EINECS(EC#)]
200-589-5 | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD00047262 | [Molecular Weight]
175.18 | [MOL File]
24297-59-4.mol |
Chemical Properties | Back Directory | [Melting point ]
168.0 to 172.0 °C | [Boiling point ]
384.5±25.0 °C(Predicted) | [density ]
1.23±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Acetone (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.31±0.10(Predicted) | [color ]
Light Orange to Dark Orange | [CAS DataBase Reference]
24297-59-4(CAS DataBase Reference) |
Hazard Information | Back Directory | [Uses]
Indol-1-yl-acetic Acid is a reactant used in the preparation of conformationally restrained analogs of pravadoline; nanomolar potent, enantioselective, (aminoalkyl)?indole agonists of the cannabinoid receptor. | [Definition]
ChEBI: An indolyl carboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by an indol-1-yl group. | [Synthesis]
Step 2: Preparation of 2-(1H-indol-1-yl)acetic acid
Ethyl 2-(1H-indol-1-yl)acetate (2.03 g, 10 mmol) was dissolved in ethanol (40 mL), aqueous sodium hydroxide solution (1 N, 50 mL) was added, and the reaction was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction solution was adjusted to slightly acidic with dilute hydrochloric acid and the mixture was subsequently concentrated under reduced pressure. The residue was extracted with ethyl acetate and the organic phase was washed with brine and the solvent was removed under reduced pressure to give pure 2-(1H-indol-1-yl)acetic acid (1.6 g, 87% yield), (LC/MS: m/z = 176.3 [M+H]+). | [References]
[1] Patent: WO2015/106025, 2015, A1. Location in patent: Paragraph 0334 [2] Patent: US2016/326123, 2016, A1. Location in patent: Paragraph 0546 [3] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 975 - 976 [4] European Journal of Medicinal Chemistry, 1989, vol. 24, p. 145 - 154 [5] Patent: WO2006/55725, 2006, A2. Location in patent: Page/Page column 188-189 |
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Energy Chemical
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