| Identification | Back Directory | [Name]
INDOLE-2-ACETIC ACID | [CAS]
32588-36-6 | [Synonyms]
2-Indolylacetic acid
INDOLE-2-ACETIC ACID
1H-INDOLE-2-ACETIC ACID
(1H-INDOL-2-YL)-ACETIC ACID
1h-indole-2-acetic acid (as sodium salt)
2-(2-indolyl)acetic acid 4-nitrophenyl ester | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD00957069 | [MOL File]
32588-36-6.mol | [Molecular Weight]
175.18 |
| Chemical Properties | Back Directory | [Melting point ]
95℃ (DEC.) | [Boiling point ]
415.0±20.0 °C(Predicted) | [density ]
1.354 | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
solid | [pka]
4.54±0.30(Predicted) | [color ]
Red-brown | [InChI]
1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13) | [InChIKey]
QOPBEBWGSGFROG-UHFFFAOYSA-N | [SMILES]
OC(CC1=CC(C=CC=C2)=C2N1)=O |
| Questions And Answer | Back Directory | [Uses]
2-Indoleacetic acid is an important pharmaceutical intermediate. Indole compounds derived from indole-2-acetic acid have various physiological effects, such as antimalarial, antitumor, and antidiabetic effects. They can be used as serotonin (HT) receptor inhibitors and cyclooxygenase inhibitors. |
| Hazard Information | Back Directory | [Chemical Properties]
off-white powder | [Synthesis]
Step 1: A solution of lithium hydroxide (346 mg, 8.25 mmol) in water (2 mL) was added to a mixture of THF (2 mL) and methanol (6 mL) of methyl 2-(1H-indol-2-yl)acetate (520 mg, 2.75 mmol) (prepared according to the method reported by Capuano et al. Chem. Ber., 1986, 119 , 2069). The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the organic solvent. The residue was diluted with water (20 mL) and extracted with ether (2 x 10 mL) to remove non-polar impurities. The aqueous phase was carefully acidified to pH 2 with 1 M HCl and then extracted with dichloromethane (3 x 20 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated under reduced pressure to give indole-2-acetic acid (350 mg, 72% yield) as a pink solid. | [References]
[1] Patent: US5814644, 1998, A |
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