80793-24-4

Basic information

• Product Name: 3-(4-NITRO-PHENYL)-PROPIONALDEHYDE
• Synonyms: 3-(4-NITRO-PHENYL)-PROPIONALDEHYDE;3-(4-Nitro-phenyl)-propionaldehyde ,98%;Benzenepropanal, 4-nitro-;3-(4-nitrophenyl)propanal
• CAS NO: 80793-24-4
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17266
• Mol File: 80793-24-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: 108 °C
• Boiling Point: 309.7°C at 760 mmHg
• Flash Point: 148.1°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 0.000627mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 3-(4-NITRO-PHENYL)-PROPIONALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-NITRO-PHENYL)-PROPIONALDEHYDE(80793-24-4)
• EPA Substance Registry System: 3-(4-NITRO-PHENYL)-PROPIONALDEHYDE(80793-24-4)

Safety Data

• Hazardous Substances Data: 80793-24-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 477, 1982 DOI: 10.1016/S0040-4039(00)86866-5

InChI:InChI=1/C9H9NO3/c11-7-1-2-8-3-5-9(6-4-8)10(12)13/h3-7H,1-2H2

Upstream product

• 1734-79-8 3-(4-nitrophenyl)-2-propenal 
• 100-13-0 4-nitrostyrene 
• 201230-82-2 carbon monoxide 
• 20716-25-0 3-(4-nitrophenyl)-1-propanol 
• 64-17-5 ethanol 
• 107-18-6 allyl alcohol 
• 30780-19-9 4-(4-nitrophenyl)butan-2-one 
• 636-98-6 p-nitrobenzene iodide 
• 35271-56-8 (E)-4-nitrocinnamyl alcohol 
• 35271-56-8 3-(4-nitrophenyl)propyl-2-en-1-ol 
• 555-16-8 4-nitrobenzaldehdye 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 637-59-2 1-Bromo-3-phenylpropane 
• 53712-77-9 1-bromo-3-(4-nitrophenyl)propane 

Downstream Products

• 104-03-0 4-nitrobenzeneacetic acid 
• 62-23-7 4-nitro-benzoic acid 
• 1309444-72-1 3-(2-aminoethyl)-5-(3-(4-nitrophenyl)propylidene)thiazolidine-2,4-dione 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 1512864-14-0 C₁₆H₁₇N₃O₄S 
• 1512864-36-6 4-(3,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)aniline 
• 1512864-32-2 C₂₁H₃₃B₂NO₆ 
• 1512864-38-8 dimethyl(3-(4-nitrophenyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)(phenyl)silane 
• 118600-23-0 2,8,14,20-tetrakis<2-(4-nitrophenyl)ethyl>pentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 
• 223438-11-7 2-(4-nitrobenzyl)prop-2-en-1-ol 

Relevant articles and documents

Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades

Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles

Pd(0) nanoparticles ca. 2 nm in diameter were obtained by the reduction of PdCl2 and Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium. The stability of Pd(0) NPs was evidenced in recycling experiments. Similar Heck coupling results were also obtained with the palladium compounds PdCl2(cod) and Pd(OAc)2 under the same conditions.