28861-29-2

Usage

Uses

Used in Organic Synthesis:
1-Diazo-4-phenyl-3-butyn-2-one is used as a reagent for the introduction of aziridine rings into functionalized organic molecules. This application is particularly relevant in the pharmaceutical and chemical industries, where aziridine-containing compounds are often sought after for their unique properties and potential applications in drug development and material science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Diazo-4-phenyl-3-butyn-2-one is used as a key intermediate in the synthesis of various drug candidates. The introduction of aziridine rings into organic molecules can lead to the development of new drugs with novel mechanisms of action and improved pharmacological profiles.
Used in Material Science:
1-Diazo-4-phenyl-3-butyn-2-one also finds application in the field of material science, where aziridine-containing compounds can be used to create new materials with unique properties. These materials may have potential uses in various industries, such as electronics, coatings, and adhesives.

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + phenylpropiolyl chloride (7299-58-3) → 1-diazo-4-phenylbut-3-yn-2-one (28861-29-2)

phenylpropiolyl chloride (7299-58-3) + diazomethyl-trimethyl-silane (18107-18-1) → 1-diazo-4-phenylbut-3-yn-2-one (28861-29-2)

Conditions	Yield
With triethylamine In acetonitrile at 0℃; for 24h; Inert atmosphere;	51 mg

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) + 1-diazo-4-phenylbut-3-yn-2-one (28861-29-2) → 4-phenyl-4-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-buta-2,3-dienoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester

Conditions	Yield
In toluene for 3.5h; UV-irradiation;	29%
In toluene for 3.5h; Photolysis;	29%

1-diazo-4-phenylbut-3-yn-2-one (28861-29-2) → 4-Phenyl-but-1-en-3-yn-1-one (138541-71-6)

Conditions	Yield
In acetonitrile Ambient temperature; Irradiation;
In 2,2,4-trimethylpentane for 0.0166667h; Wolff rearrangement; UV-irradiation;
In 2,2,4-trimethylpentane Wolff rearrangement; Photolysis;

Upstream product

• 186581-53-3 diazomethane 
• 7299-58-3 phenylpropiolyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 138541-71-6 4-Phenyl-but-1-en-3-yn-1-one 

Relevant academic research and scientific papers

Trimethylsilyldiazomethane as a versatile stitching agent for the introduction of aziridines into functionalized organic molecules

A highly enantioselective route for the introduction of aziridines into functionalized organic molecules was developed via a tandem acylation and aziridination of TMSCHN2.