N1-(4-Chlorophenyl)benzene-1,2-diamine Chemical Properties

Melting point:

117-119 °C(lit.)

Boiling point:

357.0±27.0 °C(Predicted)

Density 

1.288±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.90±0.10(Predicted)

Appearance

Brown to reddish brown Solid

InChI

InChI=1S/C12H11ClN2/c13-9-5-7-10(8-6-9)15-12-4-2-1-3-11(12)14/h1-8,15H,14H2

InChIKey

WEUBIWJPIRTWDF-UHFFFAOYSA-N

SMILES

C1(NC2=CC=C(Cl)C=C2)=CC=CC=C1N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2921599090

MSDS

• Language:English Provider:SigmaAldrich

N1-(4-Chlorophenyl)benzene-1,2-diamine Usage And Synthesis

Uses

N-(4-Chlorophenyl)-1,2-phenylenediamine is a reagent in the synthesis of clofazimine analogs as antileishmanials and antiplasmodials.

Uses

N-(4-Chlorophenyl)-1,2-phenylenediamine (2-Amino-4′-chlorodiphenylamine) was used in preparation of N-(p-chloro)phenylbenzimidazolin-2-one and monoaminophenazine dyes.

Synthesis

To a mixture of EtOH (100 ml) and NH4C1 saturated solution (15 ml), N-(4-chlorophenyl)-2-nitrobenzenamine (5.0 g, 20.1 mmol) was added, followed by iron powder (4.0 g). The reaction mixture was heated at 70 °C for 2h. The solid was filtered, and the filtrate was extracted by EA (100 mL x 3) and dried over Na2S04. After the solvent was removed, the mixture was purified by Combi-flash (PE: EA = 5 : 1) to give N1-(4-Chlorophenyl)benzene-1,2-diamine (4.1 g, 93.2 percent) as a light yellow solid.

References

[1] Chinese Journal of Chemistry, 2013, vol. 31, # 12, p. 1473 - 1482
[2] Organic Process Research and Development, 2016, vol. 20, # 2, p. 452 - 464
[3] Patent: WO2012/151512, 2012, A2. Location in patent: Page/Page column 103-104
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 145 - 150
[5] Patent: CN107445845, 2017, A. Location in patent: Paragraph 0047; 0048; 0049; 0050; 0051; 0052

N1-(4-Chlorophenyl)benzene-1,2-diamine(68817-71-0)Related Product Information

• Clofazimine
• o-Phenylenediamine
• 4-CHLORODIPHENYLAMINE
• 4-amino-4'-chlorodiphenylamine-2-sulfonic acid
• 2-AMINO-4-CHLORODIPHENYLAMINE
• 2-AMINO-4-CHLORODIPHENYLAMINE
• 4-AMINO-4'-CHLORODIPHENYLAMINE-2-SULPHONIC ACID
• 5-AMINO-2-CHLORO-10H-ACRIDIN-9-ONE
• 2-chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine
• N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE
• CLOFAZIMINE, [METHYL-3H]
• N1-(4-Chlorophenyl)benzene-1,2-diamine
• 1-(4-CHLOROPHENYL)-3-HYDROXY-1,2-DIHYDROQUINOXALIN-2-ONE