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

• 5413-05-8 ethyl 2-phenylacetoacetate 
• 941-55-9 4-toluenesulfonyl azide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 103-80-0 phenylacetyl chloride 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 71-43-2 benzene 
• 103-82-2 phenylacetic acid 
• 58929-02-5 ethyl 2,3-diphenyl-3-oxopropanoate 
• 591-50-4 iodobenzene 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 153577-30-1 (E)-ethyl phenylglyoxylate hydrazone 
• 623-73-4 diazoacetic acid ethyl ester 
• 1066-87-1 (N,N-diethylamino)tributyltin 

Downstream Products

• 7550-06-3 ethyl 2-phenyl-2-(piperidin-1-yl)acetate 
• 1013421-91-4 ethyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylacetate 
• 1013422-37-1 ethyl 2-(2-fluorophenylamino)-2-phenylacetate 
• 1013421-98-1 ethyl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate 
• 1013422-44-0 ethyl 2-(2-iodophenylamino)-2-phenylacetate 
• 1013422-53-1 ethyl 2-phenyl-2-((2,4,6-tribromophenyl)amino)acetate 
• 7554-10-1 ethyl 2-(benzamido)-2-phenylacetate 
• 1013422-06-4 ethyl 2-((3-methoxyphenyl)amino)-2-phenylacetate 
• 104411-17-8 ethyl 2-(naphthalen-1-ylamino)-2-phenylacetate 
• 5667-75-4 ethyl 2-phenyl-2-(p-tolylamino)acetateacetate 
• 6485-63-8 ethyl 2-(4-methylphenylsulfonamido)-2-phenylacetate 
• 773798-84-8 ethyl 2-(dibutylamino)-2-phenylacetate 
• 22815-54-9 ethyl 2-((2-nitrophenyl)amino)-2-phenylacetate 
• 940866-95-5 ethyl N-phenyl-α-phenylglycinate 

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.

Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides

A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates or drug candidates, scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.

Visible-light-promoted selective: O -alkylation of 2-pyridones with α-aryldiazoacetates

A visible-light-promoted O-H insertion reaction between 2-pyridones and α-aryldiazoacetates has been developed. Upon visible light irradiation, the reaction proceeds smoothly under mild and catalyst-free conditions. A wide scope of 2-pyridones and α-aryldiazoacetates are well tolerated, and various O-alkylated 2-pyridones are obtained with perfect selectivity and good functional group tolerance. A photoinduced radical process is probably responsible for the excellent selectivity. This journal is