212908-12-8

Basic information

• Product Name: Benzamide, 2-bromo-5-methoxy-N,N-dimethyl-
• CAS NO: 212908-12-8
• Molecular Formula: C10H12BrNO2
• Molecular Weight: 258.115
• Mol File: 212908-12-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzamide, 2-bromo-5-methoxy-N,N-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 2-bromo-5-methoxy-N,N-dimethyl-(212908-12-8)
• EPA Substance Registry System: Benzamide, 2-bromo-5-methoxy-N,N-dimethyl-(212908-12-8)

Safety Data

• Hazardous Substances Data: 212908-12-8(Hazardous Substances Data)

Upstream product

• 7290-99-5 N,N-dimethyl-m-methoxybenzamide 
• 22921-68-2 2-bromo-5-methoxy-benzoic acid 
• 56658-04-9 2-bromo-5-methoxybenzoyl chloride 
• 124-40-3 dimethyl amine 

Downstream Products

• 497179-52-9 6-methoxy-2-methylisoindolin-1-one 
• 77973-25-2 1-(2-dimethylaminomethyl-4-methoxyphenyl)ethanone 
• 10126-37-1 (2-bromo-5-methoxyphenyl)-N,N-dimethylmethanamine 

Relevant articles and documents

Investigation of the mechanism of C(sp3)-H bond cleavage in Pd(0)-catalyzed intramolecular alkane arylation adjacent to amides and sulfonamides

The reactivity of C(sp3)-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp3)-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction intermediate has enabled an evaluation of the reaction mechanism with a focus on the role of the bases in the C(sp3)-H bond cleaving step. The results of these stoichiometric studies, together with kinetic isotope effect experiments, provide rare experimental support for a concerted metalation-deprotonation (CMD) transition state, which has previously been proposed in alkane C(sp3)-H arylation. Moreover, DFT calculations have uncovered the additional role of the pivalate additive as a promoter of phosphine dissociation from the Pd(II) intermediate, enabling the CMD transition state. Finally, kinetic studies were performed, revealing the reaction rate expression and its relationship with the concentration of pivalate.

Simple and practical halogenation of arenes, alkenes and alkynes with hydrohalic acid/H2O2 or TBHP)

A simple protocol for the halogenation of arenes utilizing a combination of aqueous hydrogen peroxide (34 %) or tert-butylhydroperoxide (70 %) and hydrohalic acid is presented. A similar procure of oxyhalogenation involving the in situ generation of positive halogen reagents is applied for the preparation of vicinal trans-dibromoalkanes and dichloroalkanes from alkenes. The reaction of alkenes with a combination of hydrochloric acid and hydrobromic acid with hydrogen peroxide gave a mixture of 1-bromo 2-chloro alkanes and 1,2-dibromoalkanes: Oxidative bromination of alkynes is also reported under similar conditions.