1-BENZOFURAN-5-AMINE Chemical Properties

Boiling point:

259.8±13.0 °C(Predicted)

Density 

1.225±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.87±0.10(Predicted)

form 

liquid

color 

Orange

InChI

InChI=1S/C8H7NO/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5H,9H2

InChIKey

GMOLCSICTCPZCU-UHFFFAOYSA-N

SMILES

O1C2=CC=C(N)C=C2C=C1

Safety Information

Hazard Note 

Harmful

HS Code 

2932990090

1-BENZOFURAN-5-AMINE Usage And Synthesis

Uses

5-Benzofuranamine acts as a reagent in the synthesis of substituted pyrimidines as multi-targeted receptor tyrosine kinase and microtubule inhibitors as potential antitumor agents.

Definition

ChEBI: 1-Benzofuran-5-amine is a member of benzofurans.

Synthesis

Step 1. 5-Nitrobenzofuran (Compound 104, 1.89 g, 11.63 mmol), iron powder (6.5 g, 116 mmol), 36.5% hydrochloric acid (1 mL), ethanol (30 mL), and water (6 mL) were mixed, stirred, and heated to 100 °C, and the reaction was maintained for 3 hours. After completion of the reaction, the precipitate was filtered and washed with ethanol. The filtrates were combined and the solvent was removed by evaporation to give a residue. The residue was dissolved in dichloromethane (50 mL) and the organic layer was washed sequentially with aqueous sodium bicarbonate (20 mL x 2) and brine (20 mL x 1), dried over magnesium sulfate, filtered and the solvent was evaporated to afford 1-benzofuran-5-amine (Compound 105) as a brown solid (0.8 g, 51% yield).LC-MS: 134 [M + 1]+; 1H NMR ( DMSO-d6): δ 4.8 (s, 2H), 6.57 (m, 1H), 6.67 (m, 1H), 6.69 (m, 1H), 7.21 (d, J = 9.3 Hz, 1H), 7.74 (d, J = 2.4 Hz, 1H).

References

[1] Patent: US2009/76044, 2009, A1. Location in patent: Page/Page column 25

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