N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE Chemical Properties

Melting point:

145-148 °C(lit.)

Boiling point:

377.2±27.0 °C(Predicted)

Density 

1.387±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

-3.90±0.40(Predicted)

Appearance

Brown to dark brown Solid

InChI

InChI=1S/C12H9ClN2O2/c13-9-5-7-10(8-6-9)14-11-3-1-2-4-12(11)15(16)17/h1-8,14H

InChIKey

RCLKXSIRDRWUGX-UHFFFAOYSA-N

SMILES

C1(NC2=CC=C(Cl)C=C2)=CC=CC=C1[N+]([O-])=O

CAS DataBase Reference

23008-56-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2921490090

MSDS

• Language:English Provider:SigmaAldrich

N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE Usage And Synthesis

Uses

2-?Nitro-?4''-?chlorodiphenylamine is a reagent used in the synthesis of novel 4-phenoxyquinoline derivatives as c-Met kinase inhibitors. Intermediate for Clofazimine.

Preparation

4-Chlorobenzenamine and 1-Chloro-2-nitrobenzene?condensation

Synthesis

GENERAL METHOD: Suspend NaH (75 mmol) in DMF (60 mL) at 0°C and slowly add 4-chloroaniline (50 mmol). After stirring for 30 min at 0°C, a solution of 1-fluoro-2-nitrobenzene (60 mmol) in DMF (30 mL) was added dropwise. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was carefully poured into a stirred saturated NH4Cl solution (500 mL) and the precipitate was collected by filtration. The filter cake was washed with water and purified by recrystallization from methanol to give the target product N-(4-chlorophenyl)-2-nitroaniline (15h). The product was an orange solid with a yield of 72.3% and a melting point of 135.1-137.0 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.31 (s, 1H), 8.12 (d, J = 8.0 Hz, 1H), 7.53 (t, J = 7.6 Hz, 1H), 7.44 (d, J = 8.8 Hz, 2H), 7.34 (d, J = 8.8 Hz, 2H), 7.22 (d, J = 8.4 Hz, 1H), 6.93 (t, J = 7.6 Hz, 1H).MS (ESI) m/z (%): 247.2 [M-H]-.

Properties and Applications

Brilliant yellow

References

[1] Patent: CN106916069, 2017, A. Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020; 0021; 0022-0024
[2] Organic Process Research and Development, 2016, vol. 20, # 2, p. 452 - 464
[3] Molecules, 2012, vol. 17, # 4, p. 4545 - 4559
[4] Synlett, 2003, # 4, p. 564 - 566
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4475 - 4486

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