2009-96-3

Basic information

• Product Name: 1-Phenyl-2-diazo-1,3-butanedione
• Synonyms: 1-Phenyl-2-diazo-1,3-butanedione;2-Diazo-1-phenyl-1,3-butanedione;CYYVRGUWUAFEDN-UHFFFAOYSA-N
• CAS NO: 2009-96-3
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 0
• Mol File: 2009-96-3.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Phenyl-2-diazo-1,3-butanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-2-diazo-1,3-butanedione(2009-96-3)
• EPA Substance Registry System: 1-Phenyl-2-diazo-1,3-butanedione(2009-96-3)

Safety Data

• Hazardous Substances Data: 2009-96-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 195, 1991 DOI: 10.1055/s-1991-26416

Upstream product

• 6797-44-0 2-oximino-1-penyl-1,3-butanedione 
• 7664-93-9 sulfuric acid 
• 98-86-2 acetophenone 
• 1205534-16-2 2-azido-1,3-dimethylimidazolinium chloride 
• 93-91-4 1-phenylbutan-1,3-dione 
• 64-17-5 ethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 2397-79-7 2-phenyl-4H-pyran-4-one 
• 2683-06-9 3,5-dioxo-5-phenylpentanal 

Downstream Products

• 15021-43-9 dimethylsulfonium 1-benzoyl-2-oxopropylide 
• 4435-51-2 1-phenyl-butane-1,2,3-trione 
• 120242-37-7 2,2-dihydroxy-1-phenylbutane-1,3-dione 
• 32742-19-1 methyl 2-benzoylpropionate 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 16648-44-5 methyl α-acetylphenylacetate 
• 112370-88-4 2-Methoxy-3-oxo-3-phenylpropionsaeuremethylester 
• 3282-32-4 2-diazo-acetophenone 
• 124-38-9 carbon dioxide 
• 103-79-7 1-phenyl-acetone 
• 353510-66-4 3-(4-chloro-phenyl)-6-methyl-2,5-diphenyl-2,3-dihydro-[1,3]oxazin-4-one 
• 1024585-79-2 ethyl 5-chloro-1-(2-oxo-1-phenylpropyl)isoquinoline-3-carboxylate 
• 1024585-80-5 ethyl 7-bromo-1-(2-oxo-1-phenylpropyl)isoquinoline-3-carboxylate 
• 1024585-89-4 ethyl 7-methoxy-1-(2-oxo-1-phenylpropyl)isoquinoline-3-carboxylate 

Relevant articles and documents

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

Amino-modified Merrifield resins as recyclable catalysts for the safe and sustainable preparation of functionalized α-diazo carbonyl compounds

Amino-functionalized polystyrene polymers derived from Merrifield resins were prepared and characterized. These basic materials were successfully employed as heterogeneous catalysts in the diazo transfer reaction to 1,3-dicarbonyl compounds, furnishing the corresponding diazo compounds in good to excellent yields and in relatively short reaction times. In addition, the work-up and purification protocols are simple and do not generate large amounts of waste, which are important features in sustainable catalysis and environmentally benign processes. The feasibility of the recovery and reuse of the amino-modified catalysts was also verified, since they can be employed up to five times without appreciable loss of catalytic activity. This straightforward procedure can be readily scaled up to gram scale, enabling the wide application of this method. The synthetic potential was demonstrated through the two-step preparation of 2-amino-N-dodecylacetamide (ANDA), a small molecule of commercial relevance.

A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis

Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.