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

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N1-(4-Chlorophenyl)benzene-1,2-diamine Basic information
Product Name:N1-(4-Chlorophenyl)benzene-1,2-diamine
Synonyms:2-AMINO-4'-CHLORODIPHENYLAMINE;TIMTEC-BB SBB003366;N-(4-CHLOROPHENYL)-1,2-PHENYLENEDIAMINE;N-(4-chlorophenyl)benzene-1,2-diamine;(2-aminophenyl)(4-chlorophenyl)amine(SALTDATA: FREE);1,2-Benzenediamine, N-(4-chlorophenyl)-;N1-(4-Chlorophenyl)benzene-1,2-diaMine;N1-(4-Chlorophenyl)-2-amino-aniline
CAS:68817-71-0
MF:C12H11ClN2
MW:218.68
EINECS:272-391-8
Product Categories:
Mol File:68817-71-0.mol
N1-(4-Chlorophenyl)benzene-1,2-diamine Structure
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
pka4.90±0.10(Predicted)
AppearanceBrown to reddish brown Solid
InChIInChI=1S/C12H11ClN2/c13-9-5-7-10(8-6-9)15-12-4-2-1-3-11(12)14/h1-8,15H,14H2
InChIKeyWEUBIWJPIRTWDF-UHFFFAOYSA-N
SMILESC1(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
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
N1-(4-Chlorophenyl)benzene-1,2-diamine Usage And Synthesis
UsesN-(4-Chlorophenyl)-1,2-phenylenediamine is a reagent in the synthesis of clofazimine analogs as antileishmanials and antiplasmodials.
UsesN-(4-Chlorophenyl)-1,2-phenylenediamine (2-Amino-4′-chlorodiphenylamine) was used in preparation of N-(p-chloro)phenylbenzimidazolin-2-one and monoaminophenazine dyes.
SynthesisTo 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
Tag:N1-(4-Chlorophenyl)benzene-1,2-diamine(68817-71-0) Related Product Information
Clofazimine, [methyl-3H] 1-(4-Chlorophenyl)-3-hydroxy-1,2-dihydroquinoxalin-2-one N-(4-Chlorophenyl)-2-nitrobenzenamine 4-Chlorodiphenylamine 5-Amino-2-chloro-10H-acridin-9-one 4-Amino-4'-chlorodiphenylamine-2-sulphonic acid 2-Amino-4-chlorodiphenylamine 2-Amino-4-chlorodiphenylamine Clofazimine o-Phenylenediamine 4-amino-4'-chlorodiphenylamine-2-sulfonic acid 2-chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine N1-(4-Chlorophenyl)benzene-1,2-diamine