2198-54-1

Basic information

• Product Name: 3',4'-DIMETHYLACETANILIDE
• Synonyms: 3',4'-DIMETHYLACETANILIDE;3,4-DIMETHYLACETANILIDE;3',4'-Acetoxylidide;3,4-DMA;3’,4’-acetoxylidide;Acetamide, N-(3,4-dimethylphenyl)-;n-(3,4-dimethylphenyl)-acetamid;N-(3,4-Dimethylphenyl)acetamide
• CAS NO: 2198-54-1
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• EINECS: 218-597-3
• Mol File: 2198-54-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 96-98°C
• Boiling Point: 290.31°C (rough estimate)
• Flash Point: 183.6 °C
• Appearance: /
• Density: 1.0508 (rough estimate)
• Vapor Pressure: 0.000465mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.13±0.70(Predicted)
• BRN: 387706
• CAS DataBase Reference: 3',4'-DIMETHYLACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4'-DIMETHYLACETANILIDE(2198-54-1)
• EPA Substance Registry System: 3',4'-DIMETHYLACETANILIDE(2198-54-1)

Safety Data

• Statements: 22
• Safety Statements: 22-36/37-36
• RTECS: AN7500000
• Hazardous Substances Data: 2198-54-1(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic by ingestion.Questionable carcinogen with experimental tumorigenicdata. When heated to decomposition it emits toxic fumes ofNOx.

InChI:InChI=1/C10H13NO/c1-7-4-5-10(6-8(7)2)11-9(3)12/h4-6H,1-3H3,(H,11,12)

Upstream product

• 91817-69-5 3',4'-dimethylacetophenone oxime 
• 108-24-7 acetic anhydride 
• 95-64-7 4-amino-o-xylene 
• 64-19-7 acetic acid 
• 99-51-4 4-nitro-o-xylene 
• 10387-40-3 potassium thioacetate 
• 79-24-3 Nitroethane 
• 95-47-6 o-xylene 
• 31599-61-8 3,4-dimethyliodobenzene 
• 75-05-8 acetonitrile 
• 123-54-6 acetylacetone 
• 67-64-1 acetone 
• 5580-33-6 3,4-dimethylbenzamide 
• 3637-01-2 3,4-dimethylacetophenone 

Downstream Products

• 92246-61-2 4-(2-acetylamino-4,5-dimethyl-phenyl)-4-oxo-butyric acid 
• 860181-61-9 2-(2-acetylamino-4,5-dimethyl-benzoyl)-benzoic acid 
• 860747-78-0 2,5-dibromo-3,4-dimethyl-aniline 
• 106634-67-7 2-amino-4,5-dimethyl acetophenone 
• 720-50-3 acetic acid-(2-chloroacetyl-4,5-dimethyl-anilide) 
• 22058-60-2 N-(3,4-dimethyl-phenyl)-N-methyl-acetamide 
• 22364-28-9 N-(2-bromo-4,5-dimethylphenyl)acetamide 
• 1585-21-3 acetic acid-(2-chloro-4,5-dimethyl-anilide) 
• 103204-69-9 4-acetylamino-2-methylbenzoic acid 
• 857571-00-7 acetic acid-(3,4-dimethyl-5-nitro-anilide) 

Relevant articles and documents

Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides

A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

Electrochemical formation of: N, N ′-diarylhydrazines by dehydrogenative N-N homocoupling reaction

Hydrazines represent a class of compounds of high interest due to their applicability as versatile starting materials in many important transformations. Herein, we report a synthetic approach to hydrazine derivatives using commercially available anilines and an anodic dehydrogenative N-N coupling reaction as the key step.

Visible-light-induced Beckmann rearrangement by organic photoredox catalysis

A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism

Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.

An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives

A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.

Iodine and Br?nsted acid catalyzed C–C bond cleavage of 1,3-diketones for the acylation of amines

A metal-free N-acylation method of anilines with 1,3-diketones has been developed, by using iodine and p-toluene sulfonic acid as the co-catalysts. The reaction can proceed in 1,4-dioxane at elevated temperature to produce the corresponding amides with 48–89% yields. Further, the gram-scale experiment was carried out under the standard conditions and the possible mechanism was proposed.

Copper-Catalyzed Site-Selective Oxidative C?C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol

A copper-catalyzed approach for the N-acylation of anilines with acetone and acetophenones via C?C bond cleavage is described. Under the developed conditions both CHCl3 and CH2Cl2 were identified as potential C1-source to promote the transformation. The reaction features a site selective C?C bond cleavage to install the amide moieties with high functional-group compatibility and wide substrate scope. The developed method avoids the use of sensitive and narcotic agents. The method also represents an excellent complement to the previous protocols with lower E-factor (13.91 mg/1 mg) than current industrially used method (E-factor 17.54 mg/1 mg). The developed approach has also been extended for the effective preparation of pyridine derivatives and paracetamol in gram scale. The course of the reaction was monitored by 1H NMR as a preliminary investigation of the reaction mechanism. (Figure presented.).

Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature

The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.