2-AMINO-4,4'-DICHLORODIPHENYL ETHER Chemical Properties

Melting point:

61.0 to 65.0 °C

Boiling point:

234°C/27mmHg(lit.)

Density 

1.364±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

2.99±0.10(Predicted)

color 

White to Yellow to Orange

CAS DataBase Reference

121-27-7(CAS DataBase Reference)

EPA Substance Registry System

4,4'-Dichloro-2-aminodiphenyl ether (121-27-7)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2922290090

2-AMINO-4,4'-DICHLORODIPHENYL ETHER Usage And Synthesis

Chemical Properties

Brown solid

Synthesis

4,4'-Dichloro-2-nitro-diphenyl ether (12.0 g, 42.2 mmol) was used as a raw material, which was mixed with FeCl3 (702 mg, 4.33 mmol) and activated charcoal (3.70 g) in MeOH (360 mL) and stirred at 50 °C. Hydrazine monohydrate (7.00 mL, 144 mmol) was added slowly over 10 minutes, followed by heating the reaction mixture to reflux and stirring for 1 hour. After completion of the reaction, the mixture was cooled, filtered through diatomaceous earth and the filter cake was washed with MeOH. The filtrate was concentrated under reduced pressure to give an oily residue. This residue was dissolved with EtOAc, and the organic layer was washed sequentially with saturated aqueous NaHCO3 and brine, and then dried with Na2SO4. After filtration to remove the insoluble matter, the filtrate was concentrated under reduced pressure to give 5-chloro-2-(4-chlorophenoxy)-aniline (8) (10.6 g, 99% yield) as a colorless solid with a melting point of 59-61 °C. The product was characterized by 1H NMR (400 MHz, CDCl3), 13C NMR (100 MHz, CDCl3) and LC-MS (ESI) to confirm its structure.

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4952 - 4969
[2] Patent: CN107353185, 2017, A. Location in patent: Paragraph 0031; 0034; 0036
[3] Journal of the Chemical Society, 1929, p. 521
[4] Journal of the Chemical Society, 1931, p. 529,533
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 9, p. 323

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