212956-18-8

Basic information

• Product Name: N-Methoxy-N-Methyl-4-(diMethylaMino)benzaMide
• Synonyms: N-Methoxy-N-Methyl-4-(diMethylaMino)benzaMide;4-(dimethylamino)-N-methoxy-N-methylbenzamide
• CAS NO: 212956-18-8
• Molecular Formula: C₁₁H₁₆N₂O₂
• Molecular Weight: 208.25694
• Mol File: 212956-18-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Methoxy-N-Methyl-4-(diMethylaMino)benzaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methoxy-N-Methyl-4-(diMethylaMino)benzaMide(212956-18-8)
• EPA Substance Registry System: N-Methoxy-N-Methyl-4-(diMethylaMino)benzaMide(212956-18-8)

Safety Data

• Hazardous Substances Data: 212956-18-8(Hazardous Substances Data)

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 4755-50-4 4-(dimethylamino)benzoyl chloride 

Downstream Products

• 21176-94-3 4-(dimethylamino)-N-methylbenzamide 
• 1374584-18-5 (4-trifluoromethylphenyl)(4-dimethylaminophenyl)pyrid-3-yl methanol 
• 129120-25-8 (4-chlorophenyl)(4-(dimethylamino)phenyl)methanone 
• 42374-78-7 (4-(dimethylamino)phenyl)(pyridin-3-yl)methanone 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 5809-26-7 (4-dimethylamino-phenyl)-(3-hydroxy-naphthalen-2-yl)-methanone 

Relevant articles and documents

Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes

Alkylidene carbenes undergo rapid inter- and intramolecular reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of 13C-labeled precursors. Herein we report on the rearrangement of 13C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [13C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (13C{1H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally.

Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2-Containing Trisubstituted Cyclopropanes

The difluoromethyl (CHF2) group has attracted significant attention in drug discovery and development efforts, owing to its ability to serve as fluorinated bioisostere of methyl, hydroxyl, and thiol groups. Herein, we report an efficient biocat

Synthesis of various acylating agents directly from carboxylic acids

A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.

Quinolinones as Inhibitors of Translation Initiation Complex

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Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease

We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.

Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives

Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship between the substitution of the naphthalene starting materials and reactivity/selectivity is determined by several factors which act in concert: (1) the effect of substituents on the oxidation potential of the substrate, (2) the ability of the substrate to participate in a chelated copper complex which depends on (a) the inherent coordinating ability of the 3-substituent and (b) substituent steric interactions that affect chelation between the 2-hydroxyl and 3-substituent, (3) the effect of substituents on dissociation of the product from the copper catalyst.