485324-10-5

Basic information

• Product Name: N,N′-diallylbenzene-1,2-diamine
• Synonyms: N,N′-diallylbenzene-1,2-diamine
• CAS NO: 485324-10-5
• Molecular Weight: 188.272
• Mol File: 485324-10-5.mol

Chemical Properties

• CAS DataBase Reference: N,N′-diallylbenzene-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N′-diallylbenzene-1,2-diamine(485324-10-5)
• EPA Substance Registry System: N,N′-diallylbenzene-1,2-diamine(485324-10-5)

Safety Data

• Hazardous Substances Data: 485324-10-5(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 
• 95-54-5 1,2-diamino-benzene 
• 6728-21-8 allyl mesylate 
• 55899-43-9 N-allyl-1,2-phenylenediamine 

Relevant articles and documents

1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates

Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.

A highly active catalyst supported molecular sieves-NaHCO3 mixture for the selective and advantageous N-monoalkylation of amines

Amines are mono-N-alkylated by alkylmesylates in the presence of catalyst supported molecular sieves-NaHCO3 mixture in a regioselective, chemoselective and non-toxic process. Observed chemoselectivity is supported by 'DFT'.

Radical-induced formation of some siloles and diazasiloles

The Bu3Sn radical-induced reaction of o-iodobenzylvinylsilanes and o-iodoallylsilanes leads to cyclic products in yields of 40-60%. These regioselective cyclizations occur with high preference for a 5-exo and a 7-endo mode with a 6-exo mode being absent. An example for ring closure via a 7-exo mode is described.