19625-79-7

Basic information

• Product Name: N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide
• Synonyms: N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide;2-(4-Methoxy Phenyl)N,N-Dimethyl Acetamide;2-(4-METHOXY PHENYL) N,N-DIMETHYL ACETAMIDE (KG LEVEL)
• CAS NO: 19625-79-7
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.2423
• Mol File: 19625-79-7.mol

Chemical Properties

• Melting Point: 79-81 °C
• Boiling Point: 320.9 °C at 760 mmHg
• Flash Point: 147.9 °C
• Appearance: /
• Density: 1.052 g/cm³
• Vapor Pressure: 0.000308mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: Room Temperature
• PKA: -0.56±0.70(Predicted)
• CAS DataBase Reference: N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide(19625-79-7)
• EPA Substance Registry System: N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide(19625-79-7)

Safety Data

• Hazardous Substances Data: 19625-79-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide is used as an intermediate in the synthesis of α-(1-Hydroxycyclohexyl)-4-Methoxy-N,N-Dimethylbenzeneacetamide (H555555), which is a synthetic analogue of the drug Venlafaxine (Cat# V120000). Venlafaxine is a selective serotonin noradrenaline reuptake inhibitor (SNRI) that has powerful applications in the treatment of anxiety and depression. The use of N,N-Dimethyl-2-(4-methoxyphenyl)-acetamide in the synthesis of H555555 allows for the development of novel therapeutic agents with potential improvements in efficacy, safety, or pharmacokinetic properties.

InChI:InChI=1/C11H15NO2/c1-12(2)11(13)8-9-4-6-10(14-3)7-5-9/h4-7H,8H2,1-3H3

Upstream product

• 127-19-5 N,N-dimethyl acetamide 
• 696-62-8 para-iodoanisole 
• 104-01-8 4-Methoxyphenylacetic acid 
• 124-40-3 dimethyl amine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 5468-77-9 2-bromo-N,N-dimethylethanamide 
• 69519-11-5 2-(4-methoxyphenyl)-[1,3,2]-dioxaborolane 
• 824-94-2 p-methoxybenzyl chloride 
• 479486-96-9 N,N-dimethyl (trimethylsilyl)methanamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 768-60-5 4-methoxyphenylacetylen 
• 1608-24-8 3-(2,2-difluoroethenyl)anisole 

Downstream Products

• 775-33-7 4-methoxyphenethyl-dimethylamine 
• 34875-26-8 (2-(p-methoxyphenyl)ethyl)dimethylamine N-oxide 
• 130198-57-1 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclooctanol 
• 1352442-31-9 C₃₁H₂₇NO₄ 
• 1352442-29-5 C₂₅H₂₂BrNO₄ 
• 1352442-35-3 C₂₅H₂₂BrNO₄ 
• 1352442-38-6 C₂₆H₂₀BrNO₄ 
• 1352442-27-3 C₂₅H₂₃NO₄ 
• 33420-82-5 2-(4-methoxy-phenyl)-1-(4-methylsulfanyl-phenyl)ethanone 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 100-66-3 methoxybenzene 

Relevant articles and documents

Palladium-catalyzed cross-coupling reaction of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide

A Suzuki-type cross-coupling of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide in the presence of a catalytic amount of tricyclohexylphosphine as the ligand and hydroquinone as the free-radical scavenger has been demonstrated as a convenient and simple way for the synthesis of α-arylacetamide.

Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene

The continuous flow reaction of various aryl or heteroaryl bromides in toluene in the presence of THF (1.0 equiv) with sec-BuLi (1.1 equiv) provided at 25 °C within 40 sec the corresponding aryllithiums which were acylated with various functionalized N,N-

Direct defluorinative amidation-hydrolysis reaction of gem-difluoroalkenes with N,N-dimethylformamide, and primary and secondary amines

A novel and efficient method for the synthesis of arylacetamides by the reactions of gem-difluoroalkenes with N,N-dialkylformamides, and primary and secondary amines with the assistance of KOtBu and water was developed.

Amidation reaction of carboxylic acid with formamide derivative using SO3?pyridine

The amidation reaction of carboxylic acid derivatives was developed using sulfur trioxide pyridine complex (SO3?py) as a commercially available and easily handled oxidant. This method could be applied to the reaction of various aromatic and aliphatic carboxylic acids, including optically active ones, with formamide derivatives to afford the corresponding amides in good to high yields.

Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors

Oxidative amidation is a valuable process for the transformation of oxygenated organic compounds to valuable amides. However, the reaction is severely limited by the use of an expensive catalyst and limited substrate scope. To circumvent these limitations, designing a transition-metal-based nanocatalyst via more straightforward and economical methodology with superior catalytic performances with broad substrate scope is desirable. To resolve the aforementioned issues, we report a facile method for the synthesis of nanocatalysts NiO and CuO by the sol-gel-assisted thermal decomposition of complexes [Ni(hep-H)(H2O)4]SO4 (SSMP-1) and [Cu(μ-hep)(BA)]2 (SSMP-2) [hep-H = 2-(2-hydroxylethyl)pyridine; BA = benzoic acid] as single-source molecular precursors (SSMPs) for the oxidative amidation of benzyl alcohol, benzaldehyde, and BA by using N,N-dimethylformamide (DMF) as the solvent and as an amine source, in the presence of tert-butylhydroperoxide (TBHP) as the oxidant, at T = 80 °C. In addition to nanocatalysts NiO and CuO, our previously reported Co/CoO nanocatalyst (CoNC), derived from the complex [CoII(hep-H)(H2O)4]SO4 (A) as an SSMP, was also explored for the aforementioned reaction. Also, we have carefully investigated the difference in the catalytic performance of Co-, Ni-, and Cu-based nanoparticles synthesized from the SSMP for the conversion of various oxygenated and unsaturated organic compounds to their respective amides. Among all, CuO showed an optimum catalytic performance for the oxidative amidation of various oxygenated and unsaturated organic compounds with a broad reaction scope. Finally, CuO can be recovered unaltered and reused for several (six times) recycles without any loss in catalytic activity.

Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes

The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.

A novel method for the conversion of carboxylic acids to N,N-dimethylamides using N,N-dimethylacetamide as a dimethylamine source

A simple, cost effective and environmentally benign method is reported for the preparation of N,N-dimethylamides from carboxylic acids. The versatility of the method is determined by synthesising a large number of N,N-dimethylamide derivatives. Carboxylic acids are heated at 160-165°C in N,N-dimethylacetamide solvent in the presence of1,1'-carbonyldiimidazole to afford the corresponding N,N-dimethylamides in good to excellent yields.

Copper-catalyzed oxidative coupling of carboxylic acids with N,N-dialkylformamides: An approach to the synthesis of amides

A new synthetic approach for amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. A new synthetic approach to amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst and aqueous tert-butyl hydroperoxide (TBHP) as a sacrificial oxidant. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. Copyright

Continuous Method For Producing Amides Of Low Aliphatic Carboxylic Acids

The invention relates to a continuous method for producing amides, according to which at least one carboxylic acid of formula (I) R3—COON ??(I) wherein R3 is hydrogen or an optionally substituted alkyl group comprising between 1 and 4 carbon atoms, is reacted with at least one amine of formula (II) HNR1R2 ??(II) wherein R1 and R2 are independently hydrogen or a hydrocarbon group comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is then reacted to form a carboxylic acid amide, under microwave irradiation in a reaction pipe, the longitudinal axis of the pipe being oriented in the direction of propagation of the microwaves of a monomode microwave applicator.

Method For Producing Amides In The Presence Of Superheated Water

The invention relates to a method for producing carboxylic acid amides, according to which at least one carboxylic acid of formula (I) [in-line-formulae]R3—COON ??(I)[/in-line-formulae] wherein R3 is hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 50 carbon atoms, is reacted with at least one amine of formula (II) [in-line-formulae]HNR1R2 ??(II)[/in-line-formulae] wherein R1 and R2 are independently hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is reacted in the presence of superheated water, under microwave irradiation, to form a carboxylic acid amide.