20069-71-0

Basic information

• Product Name: 2-Propenamide, 3-(4-nitrophenyl)-, (2E)-
• CAS NO: 20069-71-0
• Molecular Formula: C9H8N2O3
• Molecular Weight: 192.174
• Mol File: 20069-71-0.mol

Chemical Properties

• CAS DataBase Reference: 2-Propenamide, 3-(4-nitrophenyl)-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, 3-(4-nitrophenyl)-, (2E)-(20069-71-0)
• EPA Substance Registry System: 2-Propenamide, 3-(4-nitrophenyl)-, (2E)-(20069-71-0)

Safety Data

• Hazardous Substances Data: 20069-71-0(Hazardous Substances Data)

Upstream product

• 625-77-4 N-acetylacetamide 
• 555-16-8 4-nitrobenzaldehdye 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 636-98-6 p-nitrobenzene iodide 
• 79-06-1 2-propenamide 
• 683-57-8 bromo-acetic acid amide 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 42367-53-3 3-(4-nitrophenyl)prop-2-ynamide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1597410-46-2 (E)-S-methyl 4-(4-nitrophenyl)-2-oxobut-3-enethioate 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 135879-74-2 (4-nitro-styryl)-carbamic acid methyl ester 
• 27892-88-2 (E)-4-nitrocinnamonitrile 
• 863036-58-2 3-(4-nitro-phenyl)-N-(2,2,2-trichloro-1-hydroxy-ethyl)-acrylamide 
• 863036-43-5 3-(4-nitro-phenyl)-N-[2,2,2-trichloro-1-(3-pyridin-2-yl-thioureido)-ethyl]-acrylamide 
• 863036-75-3 N-(1-amino-2,2,2-trichloro-ethyl)-3-(4-nitro-phenyl)-acrylamide 

Relevant articles and documents

Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies

We report a chemoselective, phosphine-catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n-tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with (E)-stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α-carbon and the proton on the amide nitrogen is abstracted by the ?-carbon to furnish the (E)-acrylamides. DFT calculations revealed a clear energetic driving force for the (E)- over the (Z)-isomer. (Figure presented.).

Catalytic, transition-metal-free semireduction of propiolamide derivatives: Scope and mechanistic investigation

We report a transition-metal-free trans-selective semireduction of alkynes with pinacolborane and catalytic potassium tert-butoxide. A variety of 3-substituted primary and secondary propiolamides, including an analog of FK866, a potent nicotinamide mononucleotide adenyltransferase (NMNAT) inhibitor, are reduced to the corresponding (E)-3-substituted acrylamide derivatives in up to 99% yield with >99:1 E/Z selectivity. Mechanistic studies suggest that an activated Lewis acid-base complex transfers a hydride to the α-carbon followed by rapid protonation in a trans fashion.

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.

Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides

Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.

Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one Mycobacterium tuberculosis Proteasome Inhibitors as Potential Antitubercular Agents

This is the first report of 5-styryl-oxathiazol-2-ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure-activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5-styryl-oxathiazol-2-one inhibitors identified showed little activity against replicating Mtb, but were rapidly bactericidal against nonreplicating bacteria. (E)-5-(4-Chlorostyryl)-1,3,4-oxathiazol-2-one) was most effective, reducing the colony-forming units (CFU)/mL below the detection limit in only seven days at all concentrations tested. The results suggest that this new class of Mtb proteasome inhibitors has the potential to be further developed into novel antitubercular agents for synergistic combination therapies with existing drugs.

Synthesis, characterization and catalytic activity of dinuclear half-sandwich Ru(II), Rh(III) and Ir(III) complexes

The reaction in dichloromethane between the chloro-bridged complexes [(η6-p-iPrC6H4Me) 2Ru2(μ-Cl)2Cl2], [(η5-C5Me5)2Rh 2(μ-Cl)2Cl2] and [(η5-C 5Me5)2Ir2(μ-Cl) 2Cl2], and the ligand precursor, 3,3′-[(1E, 1′E)-{(methylenebis(4,1-phenylene))bis(azanylylidene)}bis(ethan-1-yl-1- ylidene)]bis(4-hydroxy-6-methyl-2H-pyran-2-one) (LH2), has yielded the corresponding neutral dinuclear Ru(II), Rh(III) and Ir(III) complexes of the formula [{(η6-p-iPrC6H4Me)RuCl} 2L] (1), [{(η5-C5Me5)RhCl} 2L] (2) and [{(η5-C5Me5)IrCl} 2L] (3). The complexes were characterized by elemental analysis, infrared, 1H NMR, 13C NMR, ESI mass spectrometry, and complexes 2 and 3 by single-crystal X-ray structure analysis. All complexes were used as catalysts under different reaction conditions for the formation of amides from aldehydes in the presence of NH2OH·HCl and NaHCO3. All complexes show good conversion with catalytic turnover numbers up to 500.

Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction

Two new bis-imidazolinium salts (4a, 4b) have been synthesized as precursors of N-heterocyclic carbenes (NHCs) from the commercially available (R)-2,2′-dihydroxy-1,1′-binaphthalene. The two bis-imidazolinium salts were used as efficient precursor of NHC ancillary ligands in the palladium-catalyzed Heck reaction. Good to excellent yields and high stereoselectivities were obtained with ethyl acrylate, acrylonitrile, and acrylamide as starting materials. The structure of bis-imidazolinium salt 4b was further characterized by single crystal X-ray diffraction analysis. Science China Press and Springer-Verlag Berlin Heidelberg 2011.

Zinc-mediated facile synthesis of α,β-unsaturated primary amides

A general method for the synthesis of α,β-unsaturated primary amides was achieved by an one-pot, triphenylphosphine-and zinc powder-promoted Wittig reaction of bromoacetamide and aldehydes under solvent-free conditions.

Ceric ammonium nitrate (CAN) promoted efficient solid phase synthesis of amide derivatives: A green approach

Ceric ammonium nitrate (CAN) has been found to be an efficient catalyst for the solid phase synthesis of amide derivatives of a wide range of substituted carboxylic acids and urea in excellent yields under microwave irradiation conditions. High yields are achieved even on a gram scale, while reaction times are considerably shortened. This method displays both economic and environmental advantages.

Heck arylation of conjugated alkenes catalysed by a silica-supported poly-γ-methylselenopropylsiloxane palladium(0) complex, the first polymeric organoselenium palladium complex

A silica-supported poly-γ-methylselenopropylsiloxane palladium(O) complex was prepared from poly-γ-chloropropylsiloxane by treatment with sodium methyl-selenolate, followed by reaction with palladium chloride and then reduction with hydrazine hydrate. The first polymeric organoselenium palladium complex is a highly active and stereoselective catalyst for the arylation of conjugated alkenes.