2-(4-CHLOROPHENOXY)ANILINE

2-(4-CHLOROPHENOXY)ANILINE Property

Boiling point:

202°C/15mmHg(lit.)

Density 

1.260±0.06 g/cm3(Predicted)

refractive index 

1.6180-1.6220

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Oil

pka

3.69±0.10(Predicted)

color 

Colourless to Light Orange

CAS DataBase Reference

2770-11-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2922290090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-(4-CHLOROPHENOXY)ANILINE Chemical Properties,Usage,Production

Chemical Properties

pale yellow powder

Uses

Amoxapine impurity.

Synthesis

General procedure for the synthesis of 4'-chloro-2-amino-diphenyl ether from 1-(4-chlorophenoxy)-2-nitrobenzene: A mixture of commercially available iron powder (3.18 g, 57.28 mmol) and ammonium chloride (383 mg, 7.15 mmol) in ethanol (45 mL) and water (8 mL) was refluxed. To this mixture was added 1-(4-chlorophenoxy)-2-nitrobenzene (AMR01028,2.2 g, 8.81 mmol) and the resulting mixture was stirred at reflux for 1 hour. After completion of the reaction, the solvent was removed and the residue was diluted in aqueous sodium bicarbonate (40 mL) and extracted with dichloromethane (3 x 20 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and the solvent was evaporated to give 4'-chloro-2-amino-diphenyl ether (AMR01029,1.50 g, 78%) as a colorless oil, which could be used in the next step without further purification. Thin layer chromatography (TLC) Rf value was 0.53 (unfolding agent: dichloromethane).1H NMR (270MHz, CDCl3) data: δ 3.77 (2H, broad single peak, NH2), 6.71 (1H, multiple peaks), 6.83 (2H, multiple peaks), 6.89 (2H, AA'BB' system), 6.99 (1H, multiple peaks), 7.25 ( 2H, AA'BB' system).

References

[1] Patent: WO2007/3934, 2007, A2. Location in patent: Page/Page column 119
[2] Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14060 - 14067
[3] Journal of the Chemical Society, 1931, p. 529,533
[4] Journal of the Chemical Society, 1925, vol. 127, p. 2011
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1976, p. 1279 - 1285