4-METHOXY-2-CHLOROANILINE Chemical Properties

Melting point:

114℃

Boiling point:

249℃

Density 

1.234

Flash point:

105℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.26±0.10(Predicted)

Appearance

Brown to black Liquid

Safety Information

HS Code 

2921420090

4-METHOXY-2-CHLOROANILINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-chloro-4-methoxyaniline from 2-chloro-4-methoxynitrobenzene was as follows: iron powder (5.10 g, 91.69 mmol) was added to a water (22 mL) and methanol (70 mL) containing 2-chloro-4-methoxy-1-nitrobenzene (1.72 g, 9.17 mmol) and ammonium chloride (1.96 g, 36.68 mmol) in a ) in a mixed suspension. The reaction mixture was heated to 50 °C and stirred at this temperature for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the solid was washed with distilled water (2 x 15 mL). The filtrate was extracted with ethyl acetate (2 x 50 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent: 10-22% ethyl acetate/hexane) to afford 2-chloro-4-methoxyaniline (orange oil, 1.24 g, 86% yield).HPLC-MS (Method A): retention time 7.37 min; ESI-MS m/z: 158 ([M+H]+).

References

[1] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 455
[2] Patent: WO2018/1973, 2018, A1. Location in patent: Page/Page column 196
[3] Journal of the Chemical Society, 1927, p. 2218
[4] Journal of the Chemical Society, 1928, p. 331
[5] Journal of the Chemical Society, 1927, p. 2218

4-METHOXY-2-CHLOROANILINE(29242-84-0)Related Product Information

• 2'-CHLORO-4'-(TRIFLUOROMETHOXY)ACETANILIDE
• 2,6-DICHLORO-4-(TRIFLUOROMETHOXY)ANILINE
• 2-CHLORO-4-(TRIFLUOROMETHOXY)ANILINE
• Lufenuron
• 4-METHOXY-2-CHLOROANILINE
• 6-CHLORO-2,2-DIFLUORO-BENZO[1,3]DIOXOL-5-YLAMINE
• N-(2,6-DICHLORO-4-METHOXYPHENYL)ACETAMIDE
• 5-amino-2-(2,6-dichloro-4-methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one
• 2-CHLORO-4-METHOXYNITROBENZENE
• 2,6-DICHLORO-4-METHOXYANILINE
• (2-Chloro-4,6-dimethoxyphenyl)amine
• N-(7-CHLORO-2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)ACETAMIDE
• 6-CHLORO-2,2,3,3-TETRAFLUORO-7-NITRO-1,4-BENZODIOXENE
• 2-CHLORO-6-NITRO-4-(TRIFLUOROMETHOXY)ACETANILIDE
• 3,6-Dichloro-2,4-dinitrophenyl methacrylate
• 5-Amino-4-chloro-N-ethyl-2-(2-propenyloxy)benzamide
• N'1-[2-(PYRIDO[3,2-D][1,3]THIAZOL-2-YLTHIO)ACETYL]-3,5-DICHLORO-4-(3-CHLORO-4-NITROPHENOXY)BENZENE-1-SULFONOHYDRAZIDE
• 2,3,5,6-Tetrachloro-4-nitroanisole.