INDOLE-2-ACETIC ACID Chemical Properties

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

pka

4.54±0.30(Predicted)

form 

solid

color 

Red-brown

Safety Information

Hazard Codes 

Xi

HS Code 

2933998090

INDOLE-2-ACETIC ACID Usage And Synthesis

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.

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

INDOLE-2-ACETIC ACID(32588-36-6)Related Product Information

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• METHYL 3-INDOLYLACETATE
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• Methyl indole-5-carboxylate
• Indole-4-carboxylic acid
• 3-Indolepropionic acid
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