7214-61-1

Usage

Uses

Used in Chemical Production:
(1-NITROETHYL)BENZENE is used as an intermediate in the production of various chemicals for its ability to facilitate the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
(1-NITROETHYL)BENZENE is used as a precursor in the synthesis of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Dye Production:
(1-NITROETHYL)BENZENE is used as a key component in the production of dyes, enabling the creation of a variety of colorants for different applications.
Used in Pesticide Production:
(1-NITROETHYL)BENZENE is used as a chemical intermediate in the manufacturing of pesticides, playing a role in the development of agricultural chemicals to protect crops.

InChI:InChI=1/C8H9NO2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3

Upstream product

• 613-91-2 acetophenone oxime 
• 544-16-1 n-Butyl nitrite 
• 100-41-4 ethylbenzene 
• 585-71-7 (1-bromoethyl)benzne 
• 672-65-1 (1-chloroethyl)benzene 
• 79-24-3 Nitroethane 
• 3076-54-8 phenyllead(IV) triacetate 
• 25854-39-1 sodium nitroethane 
• 802294-64-0 propionic acid 
• 113747-77-6 butyl 2-nitro-2-phenylpropanoate 
• 618-36-0 rac-methylbenzylamine 
• 71-43-2 benzene 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 3756-41-0 (S)-(1-chloroethyl)benzene 

Downstream Products

• 22479-37-4 (+/-)-2,3-dinitro-2,3-dophenylbutane 
• 1481-30-7 α-Fluor-α-phenylnitroethan 
• 6196-95-8 1,2-dimethyl-4-(1-phenylethyl)benzene 
• 40390-78-1 [(1-phenylethyl)thio]benzene 
• 104330-11-2 3,3-dimethyl-2-phenyl-2-nitrobutane 
• 78176-27-9 1,1,-diphenyl-1-nitroethane 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 2912-98-3 N-(1-phenyl-ethyl)-hydroxylamine 
• 84065-83-8 1-nitro-1-(phenylsulfonyl)-1-phenylethane 
• 135921-62-9 E-2-(2-phenyl propen-1-yl) 3-nitroimidazo<1,2-a>pyridine 
• 97945-40-9 (E)-1-methyl 2-(2-phenyl propen-1-yl) 5-nitroimidazole 
• 105555-81-5 1-Methyl-5-nitro-2-((E)-2-phenyl-propenyl)-1H-imidazole 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 613-91-2 acetophenone oxime 

Relevant academic research and scientific papers

Nickel-Catalyzed NO Group Transfer Coupled with NOxConversion

Nitrogen oxide (NOx) conversion is an important process for balancing the global nitrogen cycle. Distinct from the biological NOx transformation, we have devised a synthetic approach to this issue by utilizing a bifunctional metal catalyst for producing value-added products from NOx. Here, we present a novel catalysis based on a Ni pincer system, effectively converting Ni-NOx to Ni-NO via deoxygenation with CO(g). This is followed by transfer of the in situ generated nitroso group to organic substrates, which favorably occurs at the flattened Ni(I)-NO site via its nucleophilic reaction. Successful catalytic production of oximes from benzyl halides using NaNO2 is presented with a turnover number of >200 under mild conditions. In a key step of the catalysis, a nickel(I)-?NO species effectively activates alkyl halides, which is carefully evaluated by both experimental and theoretical methods. Our nickel catalyst effectively fulfills a dual purpose, namely, deoxygenating NOx anions and catalyzing C-N coupling.

Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates

The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of ?3-nitro-substituted silyl esters containing up to two contiguous stereocenters in good yields with excellent enantioselectivities (up to 93% yield and 99:1 er). The serendipitously discovered formation of silyl ester products in this reaction demonstrates a novel platform for catalyst turnover in α,β-unsaturated acyl ammonium catalysis.

Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy

A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).

Continuous Platform to Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor

The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with the use of peracid to prepare nitroalkane substrates and the nitroalkanes themselves. In response, a continuous and scalable chemistry platform to prepare aliphatic nitroalkanes on-demand using the oxidation of oximes with peracetic acid and direct reaction of the nitroalkane intermediate in an aza-Henry reaction is reported. A uniquely designed pipes-in-series plug-flow tube reactor addresses a range of process challenges, including stability and safe handling of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane, which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors with high selectivity, thus completely avoiding isolation of the potentially unsafe low-molecular-weight nitroalkane intermediate. A continuous campaign (16 h) established that these conditions were effective in processing 100 g of the oxime and furnishing 1.4 L of nitroalkane solution.

Merging gold catalysis, organocatalytic oxidation, and Lewis acid catalysis for chemodivergent synthesis of functionalized oxazoles from: N -propargylamides

Novel catalytic systems consisting of cationic gold complexes, N-hydroxyphthalimide (NHPI), and transition-metal-based Lewis acids have been developed for the one-pot synthesis of functionalized oxazoles from N-propargylamides with excellent functional group tolerance. These transformations demonstrated the excellent compatibility of homogeneous gold catalysis with organocatalytic oxidative carbon-nitrogen bond formations using tert-butyl nitrite as the terminal oxidant. Moreover, oxazolecarbonitriles or carboxamides can be easily synthesized in a one-pot protocol according to the different synthetic requirements.

Green synthesis method for preparing nitroalkanes by oxime oxidation

The invention belongs to the field of organic chemical industries, and provides a green synthesis method for preparing nitroalkanes by oxime oxidation. At the temperature of 55 to 120 DEG C and under the pressure of 0 to 1.0 MPa, oxime, a solvent and hydrogen peroxide are reacted for 20 to 200min in the presence of certain amounts of nanoporous skeleton metal hybrid catalysts and cocatalysts, a reaction liquid is subjected to membrane separation, the catalysts can be repeatedly used for more than 7 times, and distilled to obtain nitroalkane products, the purity of the products is not less than 99%, and the yield of the products is not less than 95%. Furthermore, the green synthesis method for preparing nitroalkanes by the oxime oxidation disclosed by the invention is a green synthesis method of nitroalkanes, and suitable for large-scale industrialized production.

Micelle-enabled palladium catalysis for convenient sp2-sp3 coupling of nitroalkanes with aryl bromides in water under mild conditions

The efficacy of custom surfactant FI-750-M, designed to mimic polar solvents such as DMF and 1, 4-dioxane, has been demonstrated with the palladium-catalyzed sp2-sp3 coupling of nitroalkanes to aryl bromides using a heteroleptic palladium catalyst under unprecedentedly mild conditions. Optimized reaction conditions mostly provided good yields up to gram scale, with high selectivity and functional group tolerance for a wide scope of aryl bromides. Use of surfactant FI-750-M makes water the gross reaction medium and enables in-flask recycling. The behavior of the surfactant has been elucidated with DLS and cryo-TEM measurements, and mechanistic investigations have revealed the importance of the π-allyl ligand in the catalytic cycle.

NITRATED HYDROCARBONS, DERIVATIVES, AND PROCESSES FOR THEIR MANUFACTURE

Provided is a process for the formation of nitrated compounds by the nitration of hydrocarbon compounds with dilute nitric acid. Also provided are processes for preparing industrially useful downstream derivatives of the nitrated compounds, as well as novel nitrated compounds and derivatives, and methods of using the derivatives in various applications.

Silicon-catalyzed conversion of nitro compounds into ketones and poly(1,3-diketones)

The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions. Georg Thieme Verlag Stuttgart.

An efficient nitration of light alkanes and the alkyl side-chain of aromatic compounds with nitrogen dioxide and nitric acid catalyzed by N-hydroxyphthalimide

Nitration of light alkanes and the alkyl side-chain of aromatic compounds with NO2 and HNO3 was successfully achieved by the use of N-hydroxyphthalimide (NHPI) as a catalyst under relatively mild conditions. For example, the nitration of propane with NO2 catalyzed by NHPI at 100 °C for 14 h gave 2-nitropropane in good yield without formation of 1-nitropropane and cleaved products such as nitroethane and nitromethane. Various aliphatic nitroalkanes, which are difficult to prepare by conventional methods, could be selectively obtained by means of the present methodology by using NHPI as the key catalyst. In addition, the side-chain nitration of alkylbenzenes such as toluene was selectively carried out to lead to α-nitrotoluene without the ring nitration. The present reaction provides an efficient selective method for the nitration of light alkanes and alkylbenzenes, which has been very difficult to carry out so far.