69111-92-8

Basic information

• Product Name: 4-METHOXY-2-NITROPHENYL ACETALDEHYDE
• Synonyms: 4-METHOXY-2-NITROPHENYL ACETALDEHYDE
• CAS NO: 69111-92-8
• Molecular Formula: C₉H₉NO₄
• Molecular Weight: 195.17
• Mol File: 69111-92-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-METHOXY-2-NITROPHENYL ACETALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2-NITROPHENYL ACETALDEHYDE(69111-92-8)
• EPA Substance Registry System: 4-METHOXY-2-NITROPHENYL ACETALDEHYDE(69111-92-8)

Safety Data

• Hazardous Substances Data: 69111-92-8(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 119-25-5 4-methoxy-2-nitrobenzenediazonium chloride 
• 17484-36-5 4-Methyl-3-nitroanisole 
• 1050514-02-7 2-(4-methoxy-2-nitrophenyl)ethanol 
• 109-92-2 ethyl vinyl ether 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 1494677-57-4 C₁₃H₁₅NO₅ 
• 3189-13-7 6-methoxylindole 

Relevant articles and documents

Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction

A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.

Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts

Anilines and ethyl vinyl ether can be used as precursors for a process that is the synthetic equivalent of the α-arylation of acetaldehyde enolate. The reaction manifests a high level of functional group compatibility, allowing the ready preparation of a number of synthetically valuable compounds.

Synthesis of Substituted Indoles via Meerwein Arylation

A new method for the synthesis of substituted indoles is detailed.Meerwein arylation of 4- and 6-substituted 2-nitrobenzenediazonium chlorides with vinyl acetate or vinyl bromide and subsequent reductive cyclization of the resulting adducts affords the corresponding 6- and 4-substituted (CH3, OCH3, Cl, Br, CF3) indoles.The diazonium bisulfates of weakly basic 2-nitroanilines (4-Cl, 6-Br, 4-CF3) gave higher yields of Meerwein arylation adducts than the corresponding diazonium chlorides.Coupling of 2-nitrobenzenediazonium chloride with 2-acetoxy-1-alkenes followed byreductive cyclization affords 2-alkylindoles.