3-IODO-4-METHOXYANILINE Chemical Properties

Melting point:

74 °C

Boiling point:

321℃

Density 

1.807

Flash point:

148℃

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.24±0.10(Predicted)

color 

White to Gray to Brown

InChIKey

UHPNLGCUIGEZRB-UHFFFAOYSA-N

CAS DataBase Reference

74587-12-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2922290090

3-IODO-4-METHOXYANILINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-iodo-4-methoxyaniline from 2-iodo-4-nitroanisole: To a 250 mL round-bottomed flask were added 2-iodo-1-methoxy-4-nitrobenzene (6 g, 21.50 mmol, 1.00 eq.), iron powder (3.61 g, 64.50 mmol, 3.00 eq.), ammonium chloride (3.42 g, 63.94 mmol , 3.00 equiv), ethanol (50 mL) and water (10 mL). The reaction mixture was stirred at 85 °C for 1 hour. Upon completion of the reaction, the solid insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The brown solid product 3-iodo-4-methoxyaniline (5.35 g, 100% yield) was obtained. The product was analyzed by liquid chromatography-mass spectrometry (LC-MS): (electrospray ionization, m/z) retention time (RT) = 0.847 min, LCMS 53: m/z = 250 [M + 1].

References

[1] Patent: WO2018/118842, 2018, A1. Location in patent: Paragraph 0421-0424
[2] Patent: WO2016/199943, 2016, A1. Location in patent: Paragraph 0303
[3] Patent: WO2013/14039, 2013, A1. Location in patent: Page/Page column 45-46
[4] Patent: WO2014/152029, 2014, A2. Location in patent: Paragraph 00230
[5] Journal of the American Chemical Society, 1941, vol. 63, p. 2482,2484

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