73585-59-8

Upstream product

• 598-58-3 methyl nitrate 
• 103-65-1 phenylpropane 

Downstream Products

• 875231-51-9 1-(3-propyl-phenyl)-propan-1-one 
• 151963-09-6 3-propylbenzonitrile 
• 103858-40-8 acetic acid-(3-propyl-anilide) 
• 17171-72-1 1,3-dipropyl-benzene 
• 121-92-6 3-nitrobenzoic acid 
• 2524-81-4 3-propylaniline 

Relevant academic research and scientific papers

Poly(4-vinylpyridine)-nitrating mixture complex (PVP-NM): Solid nitrating mixture equivalent for safe and efficient aromatic nitration

Friedel-Crafts type aromatic nitration has served as an indispensable reaction within both industrial and academic applications. However, growing concern over the use of copious amounts of strong acids has prompted the search for more environmentally friendly alternatives. Polymer-bound Bronsted acids, on the other hand, have been shown useful as convenient alternatives to liquid acids. Nitric acid and sulfuric acids have, therefore, been combined, both individually and as a mixture, with poly(4-vinylpyridine). The new solid acid systems have been used to nitrate both activated and deactivated arenes under mild conditions and proved to be effective nitrating agent.

Nitration of Alkylbenzenes in Trifluoroacetic Acid

The substrate selectivity of alkylbenzene nitration with nitric acid in trifluoroacetic acid is controlled either by electronic or by steric effects of the substituents, depending the medium composition and temperature. The positional selectivity of this reaction is sterically controlled, even under electronic control of substrate selectivity.

PARA-SELECTIVE MONONITRATION OF ALKYLBENZENES UNDER MILD CONDITIONS BY USE OF BENZOYL NITRATE IN THE PRESENCE OF A ZEOLITE CATALYST

Toluene and other alkylbenzenes are mononitrated in essentially quantitative yield at ambient temperature by benzoyl nitrate in the presence of aluminium/proton exchanged large port mordenite; the reaction is highly para-selective.

Electrophilic Aromatic Nitration in the Gas Phase

Aromatic nitration by MeO+(H)NO2, in essence nitronium ion solvated by one methanol molecule, has been studied in the gas phase by using an integrated approach, based on the coordinate application of ICR, Cl, and CID mass spetrometric methods with a highly complementary radiolytic technique.The latter can be used in gases at atmospheric pressure and allows direct evaluation of key mechanistic features, in particular of substrate and positional selectivity.The results resolve early discrepancies between gas-phase and liquid-phase studies, characterizing the reaction as a typical, well-behaved electrophilic substitution of moderate selectivity.The date from the gas-phase nitration of ten monosubstituted benzenes fit a Hammett's type linear plot, characterized by a ρ value of -3.87.The correlation does not extend to highly activated substrates, such as anisole and mesitylene, since the nitration rate tends to a limiting value that cannot be increased by further enhancing the activation of the substrate, exactly as in "encounter-rate" nitrations occurring in solution.The mechanism and the energetics of the gas-phase nitration have been investigated, and the relative stability of the charged intermediates involved, in particular of the isomeric protonated nitrobenzenes, has been estimated by theoretical approaches at two different levels, using STO-3G minimal basis and 4-31G split-valence basis sets.

Aromatic Substitution. 471. Acid-Catalyzed Transfer Nitration of Aromatics with N-Nitropyrazole, a Convenient New Nitrating Agent

N-Nitropyrazole in the presence of Lewis or Bronsted acid catalysts was found to be an effective transfer nitrating agent for aromatic substrates.The nature of the acid catalyst both substrate and positional selectivies of the nitration of alkylbenzenes.No relationship was found between substrate and positional selectivities, which are considered to be determined in two separate steps.

Aromatic Substitution. 48. Boron Trifluoride Catalyzed Nitration of Aromatics with Silver Nitrate in Acetonitrile Solution

Benzene, alkylbenzenes, halobenzenes, and anisole were nitrated with silver nitrate/boron trifluoride in acetonitrile solution.Correlation of competitive rates with ?- and ?-complex stabilities indicated that the transition state of highest energy lies relatively early on the reaction coordinate.Data indicate that nitrations occur via a polarized complex of the nitrating agent, with the catalyst undergoing nucleophilic displacement by the aromatic substrate.