2-Chloro-3-methoxyaniline Chemical Properties

Melting point:

50 °C

Boiling point:

125 °C(Press: 3 Torr)

Density 

1.234±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.23±0.10(Predicted)

Appearance

Gray to brown Solid

InChI

InChI=1S/C7H8ClNO/c1-10-6-4-2-3-5(9)7(6)8/h2-4H,9H2,1H3

InChIKey

ZWPVZYDSURGWSY-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(OC)=C1Cl

2-Chloro-3-methoxyaniline Usage And Synthesis

Uses

2-Chloro-3-methoxyaniline is a reactant used in the preparation of dual inhibitors of CK2 and Pim kinases with antiproliferative activity against cancer cells.

Synthesis

General procedure for the synthesis of 2-chloro-3-methoxyaniline from 2-chloro-3-nitroanisole: 2-chloro-3-nitroanisole (1.38 g, 7.36 mmol) was dissolved in a solvent mixture of glacial acetic acid (19 mL) and acetonitrile (19 mL). To this solution was added iron powder (1.64 g, 29.4 mmol). The reaction mixture was stirred under reflux conditions for 3.5 hours. After completion of the reaction, the mixture was diluted with water (70 mL) and neutralized with solid sodium carbonate (Na2CO3). Subsequently, the product was extracted with dichloromethane (3 x 150 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the crude product 2-chloro-3-methoxyaniline (1.2 g, 100% yield) as a yellow oil. The product was used directly in the next reaction without further purification. Mass spectrometry (MS) analysis showed a molecular ion peak of 157.9 (MH)+; high performance liquid chromatography (HPLC, with TFA as additive) showed a purity of 86% at 220 nm.

References

[1] Patent: WO2004/103996, 2004, A1. Location in patent: Page 42-43
[2] Patent: WO2006/7700, 2006, A1. Location in patent: Page/Page column 62
[3] Patent: US2006/19905, 2006, A1. Location in patent: Page/Page column 25
[4] Patent: WO2006/85, 2006, A1. Location in patent: Page/Page column 77-78
[5] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 9996 - 10000

2-Chloro-3-methoxyaniline(113206-03-4)Related Product Information

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• 4-Methoxybenzylchloride
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• 4-Chloroaniline
• 2-Chloroaniline
• Bis(2-ethylhexyl)amine
• Triethanolamine
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• p-Anisidine
• o-Anisidine
• ACLONIFEN
• ANSAMITOCIN P-3
• Maytansine
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