116332-61-7

Basic information

• Product Name: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide
• Synonyms: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide;4-[Methoxy(methyl)carbamoyl]benzotrifluoride;N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide;N-Methoxy-N-methyl-4-(trifluoromethyl)
• CAS NO: 116332-61-7
• Molecular Formula: C₁₀H₁₀F₃NO₂
• Molecular Weight: 233.1871096
• Mol File: 116332-61-7.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.4710-1.4750
• CAS DataBase Reference: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide(116332-61-7)
• EPA Substance Registry System: N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide(116332-61-7)

Safety Data

• Hazardous Substances Data: 116332-61-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide is used as a potent inhibitor of the enzyme fatty acid amide hydrolase (FAAH) for studying the physiological and pathological functions of the endocannabinoid system. Its role in inhibiting FAAH makes it a potentially important tool in understanding and treating various conditions related to the endocannabinoid system.
Used in Pain Management:
In the pharmaceutical industry, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide is used as a therapeutic agent for managing pain. Its ability to inhibit FAAH can lead to increased levels of endocannabinoids, which are known to play a role in pain modulation.
Used in Inflammation Treatment:
N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide is used as an anti-inflammatory agent, leveraging its interaction with the endocannabinoid system to potentially reduce inflammation and associated symptoms.
Used in Neurological Disorders Research:
In the field of neuroscience, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide is used as a research compound to explore its potential in treating neurological disorders. Its influence on the endocannabinoid system suggests it may have applications in conditions such as multiple sclerosis, Parkinson's disease, and Alzheimer's disease.
Used in Organic Synthesis:
In the chemical industry, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide serves as a building block in organic synthesis, contributing to the development of new compounds with various applications, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 29829-22-9 S-methyldibenzothiophenium tetrafluoroborate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 132-65-0 dibenzothiophene 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 1062512-43-9 C₆H₁₈N₃O₃P 
• 14040-11-0 tungsten hexacarbonyl 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 455-13-0 4-Iodobenzotrifluoride 
• 13939-06-5 molybdenum hexacarbonyl 
• 2923-16-2 potassium trifluoroacetate 
• 187617-01-2 N,O-Dimethyl-4-iodobenzenehydroxamic acid 
• 619-58-9 4-iodobenzoic acid 
• 1711-02-0 4-iodobenzoic acid chloride 

Downstream Products

• 116332-53-7 2-<2-(4-trifluoromethylbenzoyl)ethyl>-1,3-dioxolane 
• 62587-07-9 cyclopropyl 4-(trifluoromethyl)-phenyl ketone 
• 1213551-77-9 1-cyclopropyl-1-[4-(trifluoromethyl)phenyl]methanamine 
• 115464-88-5 2-<4-(trifluoromethyl)phenyl>pyrrole 
• 117729-42-7 4-oxo-4-[4-(trifluoromethyl)phenyl]butanal 
• 1125673-98-4 (2-fluoropyridin-3-yl)(4-trifluoromethylphenyl)methanone 
• 65017-76-7 N-methyl-4-(trifluoromethyl)benzamide 
• 21084-25-3 (3-bromophenyl)-(4-trifluoromethylphenyl)methanone 
• 21084-23-1 (4-bromophenyl)(4-(trifluoromethyl)phenyl)methanone 
• 880875-41-2 2,2-dimethyl-N-(3-{[4-(trifluoromethyl)phenyl]carbonyl}-4-pyridinyl)propanamide 
• 1061304-95-7 1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 1357395-36-8 ethyl (2S)-5-(4-trifluoromethylphenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 21221-92-1 (pyridin-3-yl)(4-(trifluoromethyl)phenyl)methanone 
• 1374584-21-0 (4-(trifluoromethyl)phenyl)(4-chloro-2-fluorophenyl)pyridin-3-yl methanol 

Relevant articles and documents

Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines

Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N -methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.

Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products

A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.

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.

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

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.

Saturated Bioisosteres of ortho-Substituted Benzenes

Saturated bioisosteres of ortho-disubstituted benzenes (bicyclo[2.1.1]hexanes) were synthesized, characterized and validated. These cores were incorporated into the bioactive compounds Valsartan, Boskalid and Fluxapyroxad instead of the benzene ring. The

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

Fluoro-Substituted Methyllithium Chemistry: External Quenching Method Using Flow Microreactors

The external quenching method based on flow microreactors allows the generation and use of short-lived fluoro-substituted methyllithium reagents, such as fluoromethyllithium, fluoroiodomethyllithium, and fluoroiodostannylmethyllithium. Highly chemoselective reactions have been developed, opening new opportunities in the synthesis of fluorinated molecules using fluorinated organometallics.

TOLPERISONE ANALOGS AND METHODS OF USE

The present invention is, in part, directed to tolperisone analogs (e.g., compounds of formula (I), (I-a), (I-b), (II), (Il-a), (III), (Ill-a), (ΙΙΙ-b), (III-c), (IV), (IV-a), (V), or (V-a)) and methods of use thereof for the treatment of various conditions including elevated muscle tone and tension (e.g., spasticity, muscle spasm). In one aspect, the tolperisone analogs disclosed herein have an additional substituent at the α-position, which blocks the generation of a β- elimination product.

Magnesium Aldimines Prepared by Addition of Organomagnesium Halides to 2,4,6-Trichlorophenyl Isocyanide: Synthesis of 1,2-Dicarbonyl Derivatives

The selective addition of organomagnesium reagents to 2,4,6-trichlorophenyl isocyanide leading to magnesiated aldimines is reported. These aldimines react with Weinreb amides, ketones, or carbonates to provide the corresponding carbonyl derivatives after acidic cleavage. This allows for an efficient synthesis of 1,2-dicarbonyl compounds and α-hydroxy ketones.