Indol-1-yl-acetic acid Chemical Properties

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)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933998090

Indol-1-yl-acetic acid Usage And Synthesis

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

Indol-1-yl-acetic acid(24297-59-4)Related Product Information

• Indole
• Ethyl 2-(Chlorosulfonyl)acetate
• Indole-3-acetic acid
• Indometacin
• Indole-3-butyric acid
• INDOLE-2-ACETIC ACID
• METHYL 3-INDOLYLACETATE
• Indole-2-carboxylic acid
• 3-Indolepropionic acid
• 3-Indoleacetonitrile
• Indole-3-carbinol
• Indole-5-carboxylic acid
• Methyl indole-5-carboxylate
• Indole-4-carboxylic acid
• Methyl 1H-indole-7-carboxylate
• Indole-6-carboxaldehyde
• Methyl indole-2-carboxylate
• Methyl indole-4-carboxylate