4250-02-6

Basic information

• Product Name: 2-Propanone, 1-diazo-3-phenyl-
• CAS NO: 4250-02-6
• Molecular Formula: C9H8N2O
• Molecular Weight: 160.175
• Mol File: 4250-02-6.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: 2-Propanone, 1-diazo-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propanone, 1-diazo-3-phenyl-(4250-02-6)
• EPA Substance Registry System: 2-Propanone, 1-diazo-3-phenyl-(4250-02-6)

Safety Data

• Hazardous Substances Data: 4250-02-6(Hazardous Substances Data)

Upstream product

• 103-80-0 phenylacetyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 103-82-2 phenylacetic acid 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 4603-32-1 threo-3-Hydroxy-2,3-diphenylpropionic acid 
• 114-70-5 sodium phenylacetate 
• 186581-53-3 diazomethane 

Downstream Products

• 30911-16-1 S-ethyl 3-phenylpropionic acid thioester 
• 43026-26-2 Methanedisulfonic acid bis-(2-oxo-3-phenyl-propyl) ester 
• 69798-71-6 1-Chlor-3-phenyl-1-phenylthio-2-propanon 
• 98405-65-3 cyclohepta-2,4,6-trienylbenzylketone 
• 615-13-4 2-indanone 
• 102-04-5 1,3-Diphenylpropanone 
• 103-79-7 1-phenyl-acetone 
• 463944-14-1 3-Isopropyloxy-1-phenyl-propanon-⁽²⁾ 
• 20772-12-7 1-bromo-3-phenyl-2-propanone 
• 501-52-0 3-Phenylpropionic acid 
• 85855-49-8 1,3-diphenyl-1-phenylsulfanylpropan-2-one 
• 83397-89-1 N-butyl-2-oxo-4-phenylbutylamide 

Relevant articles and documents

Formation and fragmentation of 4-diazo-1,2-diphenyl-3-oxo-butyl acetate

Threo-4-Diazo-1,2-diphenyl-3-oxo-butyl acetate (15) could be prepared via the classical route 6 → 8 → 10 → 12 → 13 → 15. However, its alkaline hydrolysis to the bifunctional hydroxy compound 17 led to a spontaneous dehydration to the diazoketone (E)-18 and to a fragmentation to acetic acid, benzaldehyde (8) and diazoketone 19.

A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones

Chiral cyclopropane rings are key pharmacophores in pharmaceuticals and bioactive natural products, making libraries of these building blocks a valuable resource for drug discovery and development campaigns. Here, we report the development of a chemoenzymatic strategy for the stereoselective assembly and structural diversification of cyclopropyl ketones, a highly versatile yet underexploited class of functionalized cyclopropanes. An engineered variant of sperm whale myoglobin is shown to enable the highly diastereo- and enantioselective construction of these molecules via olefin cyclopropanation in the presence of a diazoketone carbene donor reagent. This biocatalyst offers a remarkably broad substrate scope, catalyzing this reaction with high stereoselectivity across a variety of vinylarene substrates as well as a range of different α-aryl and α-alkyl diazoketone derivatives. Chemical transformation of these enzymatic products enables further diversification of these molecules to yield a collection of structurally diverse cyclopropane-containing scaffolds in enantiopure form, including core motifs found in drugs and natural products as well as novel structures. This work illustrates the power of combining abiological biocatalysis with chemoenzymatic synthesis for generating collections of optically active scaffolds of high value for medicinal chemistry and drug discovery.

An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the use of any catalysts. This green protocol can be utilized for fast synthesis of various 2-aminothiazoles in good yields. [Figure not available: see fulltext.]