57999-52-7

Upstream product

• 953-26-4 ethyl 4-nitrocinnamate 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 35202-08-5 4-(4-nitrophenyl)oxetan-2-one 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 90564-32-2 3-hydroxy-3-(4-nitrophenyl)propanoic acid 
• 16642-79-8 3-(4-nitrophenyl)propionic acid 
• 1011763-39-5 3-(4-nitrophenyl)-3-phenylsulfanyl-propanoic acid 

Downstream Products

• 35202-08-5 4-(4-nitrophenyl)oxetan-2-one 
• 100-13-0 4-nitrostyrene 
• 90564-32-2 3-hydroxy-3-(4-nitrophenyl)propanoic acid 
• 102308-61-2 3-hydroxy-3-(4-nitro-phenyl)-propionic acid amide 
• 619-89-6 p-nitrocinnamic acid 
• 124-38-9 carbon dioxide 
• 10035-10-6 hydrogen bromide 
• 1028286-64-7 3-bromo-3-(4-nitro-phenyl)-propionyl chloride 
• 337964-56-4 4-bromo-1-diazo-4-(4-nitrophenyl)-2-butanone 

Relevant academic research and scientific papers

Sulphide as a leaving group: Highly stereoselective bromination of alkyl phenyl sulphides

A conceptionally novel nucleophilic substitution approach to synthetically important alkyl bromides is presented. Using molecular bromine (Br2), readily available secondary benzyl and tertiary alkyl phenyl sulphides are converted into the corresponding bromides under exceptionally mild, acid- and base-free reaction conditions. This simple transformation allows the isolation of elimination sensitive benzylic β-bromo carbonyl and nitrile compounds in mostly high yields and purities. Remarkably, protic functionalities such as acids and alcohols are tolerated. Enantioenriched benzylic β-sulphido esters, readily prepared by asymmetric sulpha-Michael addition, produce the corresponding inverted bromides with high stereoselectivities, approaching complete enantiospecificity at -40 °C. Significantly, the reported benzylic β-bromo esters can be stored without racemisation for prolonged periods at -20 °C. Their synthetic potential was demonstrated by the one-pot preparation of γ-azido alcohol (S)-5 in 90% ee. NMR studies revealed an initial formation of a sulphide bromine adduct, which in turn is in equilibrium with a postulated dibromosulphurane intermediate that undergoes C-Br bond formation.

Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions

A "ring expansion-annulation strategy" for the synthesis of substituted azulenes is described based on the reaction of β'-bromo- α-diazo ketones with rhodium carboxylates. The key transformation involves an intramolecular Buechner reaction followed by β-elimination of bromide, tautomerization, and in situ trapping of the resulting 1-hydroxyazulene as a carboxylate or triflate ester. Further synthetic elaboration of the azulenyl halide and sulfonate annulation products can be achieved by employing Heck, Negishi, Stille, and Suzuki coupling reactions. Reaction of the azulenyl triflate 84 with pinacolborane provides access to the azulenylboronate 91, which participates in Suzuki coupling reactions with alkenyl and aryl iodides. The application of these coupling reactions to the synthesis of biazulenes, terazulene 101, and related oligoazulenes is described, as well as the preparation of the azulenyl amino acid derivative 110.

A ring expansion-annulation strategy for the synthesis of substituted azulenes. Preparation and suzuki coupling reactions of 1-azulenyl triflates

(matrix presented) A new strategy for the synthesis of substituted azulenes is reported, based on the reaction of β′-bromo-α-diazo ketones with rhodium carboxylates The key transformation involves intramolecular addition of a rhodium carbenoid to an arene π-bond, electrocyclic ring opening, β-elimination, tautomerization, and trapping to produce 1-hydroxyazulene derivatives. The synthetic utility of the method is enhanced by the ability of the triflate derivatives to participate in Suzuki coupling reactions, as illustrated in a synthesis of the antiulcer drug egualen sodium (KT1-32).

Phenylmercaptotetrazolo- and nitroindazolo masked development/image modifiers

Novel nitrobenzyl compounds are incorporated into a photographic emulsion or developer for controlled release of development/image modifier compounds. This occurs imagewise only after developer oxidation products have been formed in the course of the development process. For example, nitrobenzyl-masked phenylmercaptotetrazole (PMT), incorporated into a silver halide emulsion, reacts with developer oxidation products via an electron transfer mechanism to release the potent development restrainer PMT.

A CONTRIBUTION TO MECHANISM OF ADDITION OF HYDROGEN BROMIDE TO THE α,β-UNSATURATEDSYSTEM OF 3-PHENYL-2-PROPENOIC ACID

Rate of addition of hydrogen bromide to meta- and para-substituted 3-phenyl-2-propenoic acids I was followed by polarography and UV spectroscopy.Rate of protonation either is the overall rate determining step or is at least comparable with the rate of the subsequent nucleophile attack.