22065-57-2

Basic information

• Product Name: Ethyl diazophenylacetate
• Synonyms: ETHYL DIAZOPHENYLACETATE;Ethyl 2-diazo-2-phenylacetate
• CAS NO: 22065-57-2
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.2
• Mol File: 22065-57-2.mol
• Article Data: 79

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl diazophenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl diazophenylacetate(22065-57-2)
• EPA Substance Registry System: Ethyl diazophenylacetate(22065-57-2)

Safety Data

• Hazardous Substances Data: 22065-57-2(Hazardous Substances Data)

Usage

General Description

Ethyl diazophenylacetate is a chemical compound with the molecular formula C10H11N3O2. It is an orange to brown crystalline solid that is highly sensitive to shock and friction, and must be handled with care. Ethyl diazophenylacetate is used in organic synthesis as a diazo compound, and it is commonly employed in the preparation of azo dyes and other organic compounds. Ethyl diazophenylacetate is also used as a reagent in the synthesis of various pharmaceuticals and agricultural chemicals. Due to its potential explosive nature, it is important to exercise caution when working with this compound in a laboratory setting.

InChI:InChI=1/C10H10N2O2/c1-2-14-10(13)9(12-11)8-6-4-3-5-7-8/h3-7H,2H2,1H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 591-50-4 iodobenzene 
• 993-50-0 (dimethylamino)trimethyltin 
• 1066-87-1 (N,N-diethylamino)tributyltin 
• 103-82-2 phenylacetic acid 
• 71-43-2 benzene 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 103-80-0 phenylacetyl chloride 
• 941-55-9 4-toluenesulfonyl azide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 58929-02-5 ethyl 2,3-diphenyl-3-oxopropanoate 
• 153577-30-1 (E)-ethyl phenylglyoxylate hydrazone 
• 5413-05-8 ethyl 2-phenylacetoacetate 

Relevant articles and documents

White-light emission from a structurally simple hydrazone

Two hydrazones featuring a unique excitation wavelength-dependent dual fluorescence emission have been developed. The mixing extent of the two emission bands can be modulated by tuning the excitation wavelength, resulting in multicolor and even white light emission from structurally simple hydrazones.

Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity against Mythimna separata Walker

Fraxinellone (1) is a naturally occurring degraded limonoid isolated from Meliaceae and Rutaceae plants. As a potential natural-product-based insecticidal agent, fraxinellone has been structurally modified to improve its activity. Furan ring of fraxinellone is critical in exhibiting its insecticidal activity, but with few modifications. Herein, C-ring-modified cyclopropyl analogues were semi-synthesized by Rh(II)-catalyzed cyclopropanation. The structures of the target compounds were well characterized by NMR and HRMS. The precise three-dimensional structural information of 3a was established by X-ray crystallography. Their insecticidal activity was evaluated against Mythimna separata Walker by a leaf-dipping method. Compound 3c exhibited stronger insecticidal activity than 1 and toosendanin against M. separata with teratogenic symptoms during the different periods, implying that cyclopropanation of the furan ring could strengthen the insecticidal activity of fraxinellone.

Synthesis of Functionalized Silsesquioxane Nanomaterials by Rhodium-Catalyzed Carbene Insertion into Si?H Bonds

We report carbene insertion into Si?H bonds of polyhedral oligomeric silsesquioxanes (POSS) for the synthesis of highly functionalized siloxane nanomaterials. Dirhodium(II) carboxylates catalyze insertion of aryl-diazoacetates as carbene precursors to afford POSS structures containing both ester and aryl groups as orthogonal functional handles for further derivatization of POSS materials. Four diverse and structurally varied silsesquioxane core scaffolds with one, three, or eight Si?H bonds were evaluated with diazo reactants to produce a total of 20 new POSS compounds. Novel diazo compounds containing a fluorinated octyl group and boron-dipyrromethene (BODIPY) chromophore demonstrate the use of highly functionalized substrates. Transformations of aryl(ester)-functionalized POSS compounds derived from this method are demonstrated, including ester hydrolysis and Suzuki–Miyaura cross-coupling.

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.

Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.