1H-INDOLE-3-CARBOXYLIC ACID,6-BROMO-,METHYL ESTER Chemical Properties

Boiling point:

386.2±22.0 °C(Predicted)

Density 

1.629±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Solid

pka

14.49±0.30(Predicted)

color 

Off-white to light yellow

Safety Information

HS Code 

2933998090

1H-INDOLE-3-CARBOXYLIC ACID,6-BROMO-,METHYL ESTER Usage And Synthesis

Uses

Methyl 6-bromo-1H-indole-3-carboxylate is a marine-derived natural product with antitumor activity. Methyl 6-bromo-1H-indole-3-carboxylate showed growth inhibition against Staphylococcus epidermidis, exhibiting weak or moderate minimum inhibitory concentrations (MICs)[1].

Synthesis

Intermediate Preparation: methyl 6-bromo-1H-indole-3-carboxylate; (Trimethylsilyl)diazomethane (2.0 M hexane solution, ca. 9 mL) was added dropwise to a solution of 6-bromo-1H-indole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) at room temperature, with the dropwise addition time being controlled to be within 2 minutes. After the reaction mixture took on a yellow color, it was concentrated under reduced pressure. The concentrated residue was redissolved in methanol and concentrated again under reduced pressure. This dissolution-concentration process was repeated several times to give the title compound methyl 6-bromo-1H-indole-3-carboxylate as a solid product in 100% yield.ES/MS m/e: 256.0 (M+2).

References

[1] Investigation of brominated tryptophan alkaloids from two thorectidae sponges: Thorectandra and Smenospongia

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