947590-21-8

Basic information

• Product Name: 5-chloro-N-(4-methylphenyl)-2-nitrosoaniline
• Synonyms: 5-chloro-N-(4-methylphenyl)-2-nitrosoaniline
• CAS NO: 947590-21-8
• Molecular Weight: 246.696
• Mol File: 947590-21-8.mol

Chemical Properties

• CAS DataBase Reference: 5-chloro-N-(4-methylphenyl)-2-nitrosoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-N-(4-methylphenyl)-2-nitrosoaniline(947590-21-8)
• EPA Substance Registry System: 5-chloro-N-(4-methylphenyl)-2-nitrosoaniline(947590-21-8)

Safety Data

• Hazardous Substances Data: 947590-21-8(Hazardous Substances Data)

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 106-49-0 p-toluidine 
• 932-98-9 1-chloro-4-nitroso-benzene 

Downstream Products

• 947590-27-4 4-chloro-N²-p-tolyl-o-phenylenediamine 
• 91806-09-6 N¹-(p-tolyl)benzene-1,2-diamine 
• 1447934-49-7 2,8-diethyl-4-(4-methylphenyl)-3,7-dioxo-6-propyl-3H,4H,6H,7H,8H-pyrrolo[2,3-g]quinoxaline-8-carbonitrile 
• 1447934-34-0 1-N-propyl-3-N-(4-methylphenyl)-4-nitrosobenzene-1,3-diamine 
• 32724-92-8 N-(5-chloro-2-nitrophenyl)-N-(4-methylphenyl)amine 
• 1609559-82-1 C₃₁H₂₆ClN₂P 
• 1609560-34-0 C₁₆H₁₆ClN₃ 
• 1609560-10-2 C₁₈H₂₀ClN₃ 
• 1476768-94-1 ethyl 6-chloro-2-cyano-1-hydroxy-4-(4-methylphenyl)-3-phenyl-1,2,3,4-tetrahydroquinoxaline-2-carboxylate 

Relevant articles and documents

Aryliminophosphoranes as Key Intermediates in the One-Pot Synthesis of 1-Aryl-1,3-dihydro-2H-benzimidazol-2-ones from N-Aryl-2-nitrosoanilines and Carbon Dioxide under Mild Metal-Free Conditions

A new and convenient protocol is presented for the synthesis of 1-arylbenzimidazol-2-ones by a one-pot reaction of N-aryl-2-nitrosoanilines using solid carbon dioxide as a source of the key carbonyl moiety. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The atom economy of the synthesis of the starting nitrosoanilines, accomplished by substitution of hydrogen, makes the entire synthesis of the target compounds environmentally friendly.

A short preparation of pyrroloquinoxalinones via a cascade reaction of N -aryl-5-alkylamino-2-nitrosoanilines with methyl 2-cyanoalkanoates: Unexpected direction of nucleophilic substitution of hydrogen

N-Aryl-2-nitrosoanilines possessing 5-alkylamino groups undergo a bisheteroannulation reaction with anions of 2-cyanoalkanecarboxylates resulting in pyrroloquinoxalinone derivatives. The cascade reaction involves condensation of the cyanoester anions with

Simple synthesis of N-aryl-2-nitrosoanilines in the reaction of nitroarenes with aniline anion derivatives

Anions generated from primary arylamines react with substituted nitrobenzenes to form H-adducts, which, under basic reaction conditions, undergo transformation to N-aryl-2-nitroso?amines. Competitive substitution of reactive halogens in the nit

Tautomerization of 2-nitroso-N-arylanilines by coordination as N,N'-chelate ligands to rhenium(i) complexes and the anticancer activity of newly synthesized oximine rhenium(i) complexes against human melanoma and leukemia cells in vitro

The synthesis, structural characterization and biological activity of eight ortho-quinone(N-aryl)-oximine rhenium(i) complexes are described. The reaction of the halogenido complexes (CO)5ReX (X=Cl (4), Br (5)) with 2-nitroso-N-arylanilines {(C6H3ClNO)NH(C6H4R)} (R=p-Cl, p-Me, o-Cl, H) (3a-d) in tetrahydrofurane (THF) yields the complexes fac-(CO)3XRe{(C6H3ClNO)NH(C6H4R)} (6a-d, 7a-d) with the tautomerized ligand acting as a N,N'-chelate. The substitution of two carbonyl ligands leads to the formation of a nearly planar 5-membered metallacycle. During coordination the amino-proton is shifted to the oxygen of the nitroso group which can be observed in solution for 6 and 7 by 1H NMR spectroscopy and in solid state by crystal structure analysis. After purification, all compounds have been fully characterized by their 1H and 13C NMR, IR, UV/visible (UV/Vis) and mass spectra. The X-ray structure analyses revealed a distorted octahedral coordination of the CO, X and N,N'-chelating ligands for all Re(i) complexes. Biological activity of four oximine rhenium(i) complexes was assessed in vitro in two highly aggressive cancer cell lines: human metastatic melanoma A375 and human chronic myelogenous leukemia K562. Chlorido complexes (6a and 6c) were more efficient than bromido compounds (7d and 7b) in inducing apoptotic cell death of both types of cancer cells. Melanoma cells were more susceptible to tested rhenium(i) complexes than leukemia cells. None of the ligands (3a-d) showed any significant anticancer activity.

2-Nitroso-N-arylanilines: Products of acid-promoted transformation of σH adducts of arylamines and nitroarenes

Anions generated from arylamines react with substituted nitrobenzenes to form σH adducts, which, under protonation with acetic acid, undergo transformation to 2-nitroso-N-arylamines, susceptible to reduction, condensation and cyclization reactions. Georg Thieme Verlag Stuttgart.