4374-35-0

Usage

Type of compound

Organic compound, brominated derivative of a propanone with a substituted benzene ring

Usage

Key intermediate or building block in organic synthesis and pharmaceutical research, potential applications in pharmaceuticals, agrochemicals, and material science

Versatility

Chemical structure allows for the creation of diverse molecular entities with specific properties and functions.

Upstream product

• 1201-60-1 1-(1,2-dibromopropyl)-4-methoxybenzene 
• 64-19-7 acetic acid 
• 80167-12-0 2-bromo-4-(1,2-dibromo-propyl)-anisole 
• 121-97-1 4-Methoxypropiophenone 
• 104-45-0 4-n-propylanisole 
• 104-46-1 anethole 

Downstream Products

• 4374-36-1 1-(3-bromo-4-methoxyphenyl)-1-propanone 
• 99-58-1 3-bromo-4-methoxybenzoic acid 
• 98947-18-3 2,2-dibromo-1-(3-bromo-4-methoxy-phenyl)-propan-1-one 

Relevant academic research and scientific papers

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.