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4-Amino-4'-chlorodiphenyl ether

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4-Amino-4'-chlorodiphenyl ether Basic information

Product Name:
4-Amino-4'-chlorodiphenyl ether
Synonyms:
  • 4-(4-chlorophenoxy)-benzenamin
  • 4’-chloro-4-aminobiphenylether
  • 4-chloro-4’-aminodiphenylether
  • JR-8688, 4-(4-Chlorophenoxy)benzenamine, 97%
  • p-(p-chlorophenoxy)-anilin
  • SALOR-INT L300845-1EA
  • P-(P-CHLOROPHENOXY)ANILINE
  • 4-(4'-CHLOROPHENOXY)ANILINE
CAS:
101-79-1
MF:
C12H10ClNO
MW:
219.67
EINECS:
202-976-5
Product Categories:
  • API Intermediate
  • Benzene series
  • Biphenyl & Diphenyl ether
  • Amines
  • C11 to C38
  • Nitrogen Compounds
  • Diphenyl Ethers (for High-Performance Polymer Research)
  • Functional Materials
  • Reagent for High-Performance Polymer Research
Mol File:
101-79-1.mol
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4-Amino-4'-chlorodiphenyl ether Chemical Properties

Melting point:
99-103 °C
Boiling point:
205 °C / 12mmHg
Density 
1.1764 (rough estimate)
refractive index 
1.6000 (estimate)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly, Heated)
pka
4.60±0.10(Predicted)
form 
powder to crystal
color 
White to Light yellow to Light orange
Water Solubility 
Insoluble in water.
CAS DataBase Reference
101-79-1(CAS DataBase Reference)
EPA Substance Registry System
Benzenamine, 4-(4-chlorophenoxy)- (101-79-1)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-40-43-41-37/38-22
Safety Statements 
26-36/37/39-36/37
WGK Germany 
3
RTECS 
BX1770000
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29222990

MSDS

  • Language:English Provider:ALFA
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4-Amino-4'-chlorodiphenyl ether Usage And Synthesis

Chemical Properties

Dark powder

Uses

It is used as an active pharmaceutical intermediate.

Synthesis

1836-74-4

101-79-1

General procedure for the synthesis of 4'-chloro-4-amino-diphenyl ether from 4'-chloro-4-nitro-diphenyl ether: general method: 1-substituted-4-nitrobenzene (9.3 mmol) and hydrazine hydrate (27.9 mmol) were dissolved in 20 mL of ethanol, and stirred for 10 min at 28-30°C. The reaction was carried out in aqueous suspension of Raney-Ni (0.02 g). An aqueous suspension of Raney-Ni (0.02 g, 4.41 mL) was added in three 10-min intervals. after 30 min, the reaction was allowed to plateau, and the temperature was raised to 50-60 °C to continue stirring for 6 h. The catalyst was removed by filtration. After completion of the reaction, the catalyst was removed by filtration. The solvent was removed by evaporation to give the target product 4'-chloro-4-amino-diphenyl ether.

References

[1] Green Chemistry, 2017, vol. 19, # 14, p. 3400 - 3407
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1588 - 1592
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4811 - 4815
[4] Pharmazie, 1980, vol. 35, # 2, p. 78 - 80
[5] Pharmazie, 1980, vol. 35, # 2, p. 78 - 80

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