2,4-Dichloro-5-methoxyaniline Chemical Properties

Melting point:

51 °C

Boiling point:

290.1±35.0 °C(Predicted)

Density 

1.375±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

1.59±0.10(Predicted)

color 

Pale Brown

InChIKey

AJROJTARXSATEB-UHFFFAOYSA-N

CAS DataBase Reference

98446-49-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

UN2810

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

2922290090

2,4-Dichloro-5-methoxyaniline Usage And Synthesis

Uses

2,4-Dichloro-5-methoxyaniline is mainly used to prepare bosutinib intermediate 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-(3-chloropropoxy)-3-quinolinecarbonitrile

Synthesis

2,4-Dichloro-5-methoxyaniline is mainly used to prepare bosutinib intermediate 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-(3-chloropropoxy)-3-quinolinecarbonitrile

Synthesis

General procedure for the synthesis of 2,4-dichloro-5-methoxyaniline from N-(2,4-dichloro-5-methoxyphenyl)acetamide: N-(2,4-dichloro-5-methoxyphenyl)acetamide (100.7 g, 0.43 mol) was suspended in a mixture of ethanol (500 g), water (500 g), and concentrated hydrochloric acid (300 g, 3 mol), stirred and heated to 70 °C and the reaction lasted for 12 h to obtain a brown solution. After completion of the reaction, ethanol (about 200 g) was evaporated under reduced pressure and the remaining mixture was stirred and cooled to room temperature. After standing for 2 h, the precipitated solid was collected by filtration, washed with water (2 x 200 g) and dried under vacuum at 35 °C to afford 2,4-dichloro-5-methoxyaniline (69.4 g, 84% yield) as a light tan solid with a melting point of 49.5-51.1 °C (literature value 50.5-51.5 °C). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (EI): 1H NMR δ= 3.76 (s, 3H), 5.13 (br s, 2H), 6.58 (s, 1H), 7.23 (s, 1H); mass spectrum (EI) m/z (relative abundance) = 191 (100).

References

[1] Synthesis (Germany), 2015, vol. 47, # 20, p. 3133 - 3138
[2] Journal of the American Chemical Society, 1919, vol. 41, p. 460

2,4-Dichloro-5-methoxyaniline(98446-49-2)Related Product Information

• p-Anisaldehyde
• Anisole
• 3-Ethoxyaniline
• 2,4-Dimethoxyaniline
• (Trifluoromethoxy)benzene
• 4-(Trifluoromethoxy)aniline
• 4-Aminoveratrole
• p-Anisidine
• 4-Methoxybenzoic acid
• 4-Methoxyphenol
• 4-Methoxybenzylchloride
• 2-CYANO-N-(2,4-DICHLORO-5-METHOXYPHENYL) ACETAMIDE
• Bosutinib Impurity
• Bosutinib Impurity 15
• Bosutinib Impurity 6
• 4-CHLORO-7-HYDROXY-6-METHOXY-QUINOLINE-3-CARBONITRILE
• Bosutinib Impurity 4
• 1,3-diisopropylurea