85937-41-3

Basic information

• Product Name: 2-Butanone, 4-[(4-chlorophenyl)amino]-
• CAS NO: 85937-41-3
• Molecular Formula: C10H12ClNO
• Molecular Weight: 197.664
• Mol File: 85937-41-3.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 4-[(4-chlorophenyl)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 4-[(4-chlorophenyl)amino]-(85937-41-3)
• EPA Substance Registry System: 2-Butanone, 4-[(4-chlorophenyl)amino]-(85937-41-3)

Safety Data

• Hazardous Substances Data: 85937-41-3(Hazardous Substances Data)

Upstream product

• 5465-90-7 N-(4-chlorophenyl)glycine 
• 67-64-1 acetone 
• 106-47-8 4-chloro-aniline 
• 78-94-4 methyl vinyl ketone 
• 590-90-9 1-Hydroxy-3-butanone 
• 598-32-3 2-hydroxy-3-butene 
• 627-27-0 homoalylic alcohol 
• 50-00-0 formaldehyd 
• 116-11-0 2-Methoxypropene 
• 3299-38-5 4-(diethylamino)butan-2-one 
• 20265-96-7 p-chloroaniline hydrochloride 

Relevant articles and documents

Iron powder and tin/tin chloride as new reducing agents of Meerwein arylation reaction with unexpected recycling to anilines

Simple and rapid route for Meerwein arylation reaction using iron powder or a mixture of tin/tin chloride has been developed. In the presence of iron powder, different aryl diazonium salts reacted with methyl vinyl ketone, acrylates, and isopropenyl acetate. Production of oximes was detected as the main product with acrylates or in a mixture with β-aryl methyl ketones in the case of methyl vinyl ketone. The in situ produced HNO2 from an excess of NaNO2/HCl was trapped by alkyl aryl radical to form oximes in the E configuration form. The presence of tin/tin chloride mixture in the reaction of the aryl diazonium salts with methyl vinyl ketone produced Michael products along with β-aryl methyl ketones. The predicted α-aryl methyl ketones from the reaction of isopropenyl acetate with the diazotized anilines were obtained using iron or tin/tin chloride mixture.

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.

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.