6220-79-7

Basic information

• Product Name: 2-Butanone, 4-(phenylamino)-
• CAS NO: 6220-79-7
• Molecular Formula: C10H13NO
• Molecular Weight: 163.219
• Mol File: 6220-79-7.mol

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 4-(phenylamino)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 4-(phenylamino)-(6220-79-7)
• EPA Substance Registry System: 2-Butanone, 4-(phenylamino)-(6220-79-7)

Safety Data

• Hazardous Substances Data: 6220-79-7(Hazardous Substances Data)

Upstream product

• 598-32-3 2-hydroxy-3-butene 
• 62-53-3 aniline 
• 627-27-0 homoalylic alcohol 
• 103-01-5 N-Phenylglycine 
• 67-64-1 acetone 
• 590-90-9 1-Hydroxy-3-butanone 
• 3204-31-7 1,3-Dimethyl-2,3-dihydro-1H-benzoimidazole 
• 78-94-4 methyl vinyl ketone 
• 5099-95-6 1-phenylazetidin-2-one 
• 74204-92-5 3-methyl-1-phenyl-1,4,5,6-tetrahydropyridazine 
• 3299-38-5 4-(diethylamino)butan-2-one 
• 142-04-1 aniline hydrochloride 
• 99359-66-7 N-(3-chloro-but-2-enyl)-aniline 
• 69611-44-5 N-(3-methyl-2-butyne)aniline 

Downstream Products

• 154825-69-1 2-Methyl-4-phenylaminobutan-2-ol 
• 604-49-9 4-methyl-5,6-benzoquinoline 
• 518036-34-5 N-(3-oxo-butyl)-acetanilide 
• 22613-86-1 4-anilino-2-butanol 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 18833-98-2 4-[N-(2-hydroxy-ethyl)-anilino]-butan-2-one 

Relevant articles and documents

Biocatalytic Aza-Michael Addition of Aromatic Amines to Enone Using α-Amylase in Water

The Michael addition of amines with enones for synthesizing β-amino carbonyls constitutes a valuable transformation in organic chemistry. While various catalyst have been made available for catalyzing the Michael addition of aromatic amines to enones but

Method for generating beta-amino ketone compounds through iodine catalysis

The invention discloses a method for generating beta-amino ketone compounds by catalyzing 4-hydroxy-2-butanone to react with aromatic amine through iodine. The method comprises the following steps: taking 4-hydroxy-2-butanone and different aromatic amines as reaction substrates, taking iodine as a catalyst, and dimethyl sulfoxide or N,N-dimethyl formamide as a solvent, and reacting at room temperature in a nitrogen atmosphere to obtain the beta-amino ketone compounds, wherein other byproducts are undetected. By adopting the preparation method disclosed by the invention, the beta-amino ketone compounds can be generated by catalyzing 4-hydroxy-2-butanoe to react with aromatic amine through the iodine at room temperature for the first time.

Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones

An iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to yield β-aminoketones and benzo[h]quinolones had been developed. Noble metallic catalysts, oxidants, α β-unsaturated ketone intermediates and aza-Michael addition were not involved in this coupling reaction which made it unique when compared to other reactions reported in literature. Inexpensive iodine catalyst, easy accessible raw materials, mild reaction conditions, good functional group tolerance and excellent selectivity made this coupling reaction be a practical method. This reaction can also be scaled up.

Method for catalyzing N-alkylation reaction by TEMPO and TBN

The invention discloses a method for catalyzing N-alkylation reaction of aniline and 4-hydroxy-2-butanone by TEMPO and TBN. 4-hydroxy-2-butanone and different anilines are used as the reaction substrate, TEMPO (2,2,6,6-tetramethylpiperidine oxide) is used as catalyst, TBN (tert-butyl nitrite) is used as cocatalyst, dimethyl sulfoxide or N,N-dimethylformamide or toluene is used as solvent, N-alkylation product is obtained in nitrogen atmosphere at room temperature, no other by-products are detected. The preparation method of the invention uses TEMPO and TBN to catalyze aniline compounds and 4-hydroxy-2-butanone to perform N-alkylation reaction.

TBN-Catalyzed Dehydrative N-Alkylation of Anilines with 4-Hydroxybutan-2-one

Until now, the substitution of alcohols by N-nucleophiles via TBN-catalyzed dehydrogenation was not known. Herein, we reported a TBN catalyzed dehydrative N-alkylation of anilines with 4-hydroxybutan-2-one in the presence of TEMPO, which was different from the TEMPO/TBN catalyzed oxidation reactions. A range of anilines reacted successfully with 4-hydroxybutan-2-one to generate the N-monoalkylation products in good yields. Mechanistic studies revealed that this reaction most possibly proceeded through aza-Michael addition. Water was the only by-product, making it more environmentally friendly. The gram-scale reactions verified the synthetic practicality of this protocol.

TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole

TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.

Palladium-catalyzed aerobic oxidative coupling of allylic alcohols with anilines in the synthesis of nitrogen heterocycles

We report herein an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones. Further, we explored the synthetic utility of β-amino ketones through an intramolecular α-arylation methodology and a one-pot domino annulation, thereby providing rapid access to indolines and quinolines.

Cobalt-Porphyrin-Catalyzed Intramolecular Buchner Reaction and Arene Cyclopropanation of In Situ Generated Alkyl Diazomethanes

Cobalt(II)-porphyrin catalyzed intramolecular Buchner reaction and arene cyclopropanation of alkyl diazomethanes generated in situ from N-tosylhydrazones gave a range of bicyclic cycloheptatriene fused pyrrolidines and tetracyclic cyclopropane fused pyrro

Palladium-catalyzed oxidative amination of homoallylic alcohols: Sequentially installing carbonyl and amino groups along an alkyl chain

A novel Pd-catalyzed intermolecular cascade oxidative amination of homoallylic alcohols to yield β-amino ketones has been developed by using TBHP as the terminal oxidant. The synthetic utility of the reaction can be performed by installing the carbonyl an

A photoredox catalyzed radical-radical coupling reaction: Facile access to multi-substituted nitrogen heterocycles

Visible light induced photoredox catalysis is an efficient method for radical activation. Herein, we report the photoredox catalysis involving an intramolecular radical-radical coupling reaction that proceeds through a biradical intermediate. This protocol represents a new synthetic route to construct multi-substituted N-heterocycles. Four, five and six-membered N-heterocyclic structures with a quaternary carbon center are accessible under mild conditions.