4-(CHLORO-DIFLUORO-METHOXY)-PHENYLAMINE Chemical Properties

Boiling point:

231.9±40.0 °C(Predicted)

Density 

1.402±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), DMSO (Sparingly)

pka

4.04±0.10(Predicted)

form 

liquid

color 

Pale yellow

InChI

InChI=1S/C7H6ClF2NO/c8-7(9,10)12-6-3-1-5(11)2-4-6/h1-4H,11H2

InChIKey

QDTUQGSYECRXDO-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(OC(Cl)(F)F)C=C1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-43-22

Safety Statements 

26-36/37/39-36/37

Hazard Note 

Irritant

HS Code 

2921420090

4-(CHLORO-DIFLUORO-METHOXY)-PHENYLAMINE Usage And Synthesis

Uses

4-Chlorodifluoromethoxyaniline has been used as a reactant for the preparation of arylphthalazines as a potent and orally bioavailable inhibitor of VEGFR-2.

Synthesis

General procedure for the synthesis of 4-(chlorodifluoromethoxy)aniline from 1-(chlorodifluoromethoxy)-4-nitrobenzene: 167 g of 1-(chlorodifluoromethoxy)-4-nitrobenzene was added to an autoclave, followed by the addition of 200 g of ethyl acetate and 15 g of nickel Nguyenne. After changing to a nitrogen atmosphere, hydrogen was introduced and the pressure in the autoclave was maintained at 2~3 MPa, and the reaction temperature was controlled at 30-40 °C. After the system pressure was stabilized and no longer decreased, the reaction was continued for 1 hour. Upon completion of the reaction, samples were taken and analyzed to ensure that the residual nitro compounds in the hydrogenation reaction solution were less than 0.5%. Subsequently, the catalyst was removed by filtration, and most of the solvent was firstly recovered by distillation at atmospheric pressure, and then purified by decompression distillation, finally 92.6 g of 4-(chlorodifluoromethoxy)aniline was obtained with a yield of 64.2%.

References

[1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 2, p. 269 - 271
[2] Green Chemistry, 2018, vol. 20, # 1, p. 130 - 135
[3] Patent: CN104119238, 2016, B. Location in patent: Paragraph 0018; 0032; 0033; 0037; 0038

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