90359-80-1

Basic information

• Product Name: Benzamide, 2-bromo-N,N-diethyl-6-methyl-
• CAS NO: 90359-80-1
• Molecular Formula: C12H16BrNO
• Molecular Weight: 270.169
• Mol File: 90359-80-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzamide, 2-bromo-N,N-diethyl-6-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 2-bromo-N,N-diethyl-6-methyl-(90359-80-1)
• EPA Substance Registry System: Benzamide, 2-bromo-N,N-diethyl-6-methyl-(90359-80-1)

Safety Data

• Hazardous Substances Data: 90359-80-1(Hazardous Substances Data)

Upstream product

• 90259-31-7 2-bromo-6-methylbenzoic acid 
• 109-89-7 diethylamine 
• 85370-86-1 N,N-diethyl-2-benzamide 
• 85370-79-2 N,N-diethyl-2-(trimethylsilyl)-6-benzamide 
• 85370-87-2 N,N-diethyl-2-<(trimethylsilyl)methyl>benzamide 
• 62924-92-9 N,N-diethyl-2-(trimethylsilyl)benzamide 
• 2728-04-3 N,N-diethyl-ortho-toluamide 
• 1696-17-9 N,N-diethylbenzamide 
• 85370-65-6 N,N-diethyl-2-methyl-6-(trimethylsilyl)benzamide 

Downstream Products

• 2728-04-3 N,N-diethyl-ortho-toluamide 
• 1093239-40-7 N,N-diethyl-2-methyl-6-(2-toluidino)benzamide 

Relevant articles and documents

Nickel-catalyzed reductive defunctionalization of esters in the absence of an external reductant: Activation of C-O bonds

The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C-O bond in O-Alkyl esters is reported. Various groups, such as N-containing heterocycles, esters, amides, and even arene rings can function as a directing group.

Directed Ortho Metalation of N,N-Diethylbenzamides. Silicon Protection of Ortho Sites and the o-Methyl Group

New general methodology of value in aromatic chemistry based on silicon protection of preferred ortho metalation sites in benzamides and o-methyl groups in o-toluamides (1, 2, Scheme I) is described.According to these methodologies, routes (Scheme II and V) to 1,2,5-, 1,2,4,5-, and 1,2,3-substituted aromatics with a variety of functionalities and oxidation states have been developed (Tables I and II).These tactics are used for the synthesis of difficult to access halo (10a-b, Scheme III) and methyl (21,25, Scheme VI) heterocycles.Ipso bromodesilylation reactions with bromine lead regiospecifically to o-bromobenzamides (12a,c, 14, Scheme IV).Walk-around-the-ring metalation processes provide highly substituted aromatics 27, 28, 29, and 30 (Scheme VII); the X-ray structure of the hexasubstituted derivative 30 shows a significant puckering of the aromatic ring.Cesium fluoride induced carbodesilylation of o-silylbenzamides with benzaldehyde affords, after TsOH cyclization, phthalides (31a-c, Scheme VIII) and constitutes a neutral alternative to the directed ortho metalation approach. α- and α,α-silylated o-toluamides are used in fluoride-mediated carbodesilylation (34a,d, Scheme IX) and desilylative Peterson olefination (35, Scheme X) procedures, respectively.The utility of α-silylated o-toluamide for the synthesis of a tetralin (38, Scheme XI) via an o-quinodimethane species is given.