219492-11-2

Basic information

• Product Name: 2-(benzyloxy)-1-methyl-4-nitrobenzene
• Synonyms: 2-(benzyloxy)-1-methyl-4-nitrobenzene
• CAS NO: 219492-11-2
• Molecular Weight: 243.262
• Mol File: 219492-11-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(benzyloxy)-1-methyl-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(benzyloxy)-1-methyl-4-nitrobenzene(219492-11-2)
• EPA Substance Registry System: 2-(benzyloxy)-1-methyl-4-nitrobenzene(219492-11-2)

Safety Data

• Hazardous Substances Data: 219492-11-2(Hazardous Substances Data)

Upstream product

• 5428-54-6 2-methyl-5-nitrophenol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 24224-30-4 2-hydroxy-3-methyl-9H-carbazole 
• 25488-37-3 mahanimbidine 
• 21104-28-9 mahanimbine 
• 27300-29-4 3',3'-dimethylpyrano[3,2-a]carbazole-3-carbaldehyde 
• 23095-44-5 girinimbine 
• 219492-12-3 3-(benzyloxy)-4-methylaniline 
• 89882-69-9 N-(3-(benzyloxy)-4-formylphenyl)acetamide 

Relevant articles and documents

Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes

A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.

Efficient construction of pyrano [3, 2-a]carbazoles: Application to a biomimetic total synthesis of cyclized monoterpenoid pyrano [3, 2-a]carbazole Alkaloids

We have developed a highly efficient route to 2-hydroxy-3-methyl-carbazole (1) via a palladium-catalyzed construction of the carbazole skeleton. Using 1 as relay compound, different methods for annulations of pyran rings by reaction with terpenoid building blocks have been tested. The Lewis acid promoted reaction of 1 with prenal (21) opened up an efficient route to girinimbine (3) and the corresponding reaction with citral (25) afforded mahanimbine (5). Oxidation of compounds 3 and 5 provided murraya-cine (4) and murrayacinine (6). Following the biogenetic proposal, mahanim-bine (5) has been exploited for efficient biomimetic syntheses of the cyclized monoterpenoid pyrano[3, 2-a]carbazole alkaloids cyclomahanimbine (7), maha-nimbidine (8) and bicyclomahanimbine (9). The interconversions of 5, 7, 8 and 9 are described and mechanistic implications are discussed. Structural assignments are unambiguously verified by X-ray crystal structure determinations. Moreover, cyclomahanimbine (7) was transformed into murrayazolinine (10) and exozoline (11).