75414-82-3

Basic information

• Product Name: ethyl 2-diazo-3-(4-nitrophenyl)-3-oxopropanoate
• Synonyms: ethyl 2-diazo-3-(4-nitrophenyl)-3-oxopropanoate
• CAS NO: 75414-82-3
• Molecular Weight: 263.21
• Mol File: 75414-82-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: ethyl 2-diazo-3-(4-nitrophenyl)-3-oxopropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-diazo-3-(4-nitrophenyl)-3-oxopropanoate(75414-82-3)
• EPA Substance Registry System: ethyl 2-diazo-3-(4-nitrophenyl)-3-oxopropanoate(75414-82-3)

Safety Data

• Hazardous Substances Data: 75414-82-3(Hazardous Substances Data)

Upstream product

• 838-57-3 ethyl 4-nitrobenzoylacetate 
• 239094-37-2 ethyl-2-diazo-3-hydroxy-3-(4-nitrophenyl)-propanoate 

Downstream Products

• 1364737-01-8 4-ethyl 3-methyl 2-(dimethylamino)-5-(4-nitrophenyl)furan-3,4-dicarboxylate 
• 1287721-35-0 methyl 2-{(2-ethoxy-1-(4-nitrobenzoyl)-2-oxoethyl)[(2,2,2-trichloroethoxy)carbonyl]amino}-3-(phenylthio)acrylate 

Relevant articles and documents

Solvent-Directed Transition Metal-Free C-C Bond Cleavage by Azido-1,3,5-triazines and Their Stability-Reactivity Paradox

We report a solvent-directed and regioselective carbon-carbon bond cleavage of aryl ketones by azido-1,3,5-triazines (ATs), which is typically completed within 10 min in DMSO at room temperature, without using transition metal catalysts. The cleavage is driven by the steric hindrance in the adducts of aryl ketones and ATs, which is substantiated by DFT calculation. Our recent results showed that ATs present high reactivity in solution and high stability in solid state. This "stability-reactivity paradox"has been explained in light of the molecular and crystal structures of ATs.

Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds

We report a crystalline compound 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) as an intrinsically safe, highly efficient, and shelf-stable diazo-transfer reagent. Because the decomposition of ADT is an endothermal process (ΔH = 30.3 kJ mol-1), ADT is intrinsically nonexplosive, as proved by thermal, friction, and impact tests. The diazo-transfer reaction based on ADT gives diazo compounds in excellent yields within several minutes at room temperature. ADT is very stable upon >1 year storage under air at room temperature.

Amine-mediated synthesis of amides from 1,3-dicarbonyl compounds through a domino diazo transfer/aminolysis process

The dual role of amines as both catalysts and substrates for the synthesis of diazo compounds or carboxamides from 1,3-dicarbonyl compounds is described herein. In the presence of a suitable diazo transfer agent, primary and cyclic secondary amines act as basic catalysts for the diazo transfer reaction to malonates, β-keto esters, and β-diketones. Depending on the structure of the 1,3-dicarbonyl compound and the nucleophilicity of the amine, the resulting α-diazo-β-keto ester undergoes cleavage of the acyl group to give amides. A multifunctionalized γ-azido-α-diazo-β-keto ester was cleanly prepared in good yields by this one-pot protocol under practical and safe conditions, being employed in a Knoevenagel-type condensation with aromatic aldehydes to give densely functionalized diazo azido compounds. Further treatment of these unsaturated γ-azido-α-diazo-β-keto esters with primary amines readily furnished the corresponding α-azidocinnamamides in high yields, which were used in the synthesis of novel indole-2-carboxamides through the rhodium-catalyzed intramolecular C–H insertion.