603-71-4

Usage

Uses

Used in Pharmaceutical Industry:
2-NITROMESITYLENE is used as a key intermediate in the synthesis of pharmaceutical compounds for the prevention and/or treatment of various diseases. Its unique chemical structure allows it to be a building block for the development of new drugs with potential therapeutic benefits.
Used in Functional Healthy Food Industry:
2-NITROMESITYLENE is used as an active ingredient in functional healthy food products, where it may contribute to the prevention or management of certain health conditions. Its presence in these products is based on its potential health-promoting properties, which can be attributed to its chemical structure and interactions with biological systems.

Purification Methods

Crystallise it from EtOH, or a small volume of MeOH and cool in an ice-salt bath (m 43.5o). [Powell & Johnson Org Synth Coll Vol II 449 1943, Beilstein 5 H 410, 5 III 923, 5 IV 1028.]

InChI:InChI=1/C9H11NO2/c1-6-4-7(2)9(10(11)12)8(3)5-6/h4-5H,1-3H3

Upstream product

• 108-67-8 1,3,5-trimethyl-benzene 
• 1194-65-6 2,6-dichloro-benzonitrile 
• 88-05-1 2,4,6-trimethylaniline 
• 7697-37-2 nitric acid 
• 1196-12-9 2-nitrosomesitylene 
• 7732-18-5 water 
• 75-52-5 nitromethane 
• 940-93-2 2,4,6-trimethylpyrylium chlorate(VII) 
• 139139-80-3 bis(2,4,6-trimethylphenyl)iodonium triflate 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 13021-15-3 2,4,6-trimethyl-N,N-dimethylaniline 
• 603-71-4 nitromesitylene 
• 120-12-7 anthracene radical anion 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 3095-38-3 3,5-dimethyl-4-nitrobenzoic acid 
• 18515-18-9 3,5-dimethyl-4-nitrobenzaldehyde 
• 713147-74-1 3,5-dimethyl-2-nitrobenzaldehyde 
• 14353-69-6 N-mesityl-hydroxylamine 
• 19625-68-4 2-nitro-1,3,5-benzenetricarboxylic acid 
• 88-05-1 2,4,6-trimethylaniline 
• 5692-66-0 2,2',4,4',6,6'-hexamethylazobenzene 
• 854752-52-6 N-isopentyl-2,4,6-trimethyl-aniline 
• 2958-62-5 mesityl isocyanate 
• 6095-81-4 N,N'-di(2,4,6-trimethylphenyl)urea 
• 20488-59-9 anti-2,2',4,4',6,6'-Hexamethylazobenzene 
• 29418-29-9 p-Tolyl-(2,4,6-trimethyl-phenyl)-diazene 
• 501-60-0 (E)-4,4'-dimethylazobenzene 
• 21650-51-1 (E)-bis(4-chlorophenyl)diazene 

Relevant academic research and scientific papers

The Inhibiting Effects of Tetraalkylammonium Cations on Simple Heterogeneous Electron Transfer Reactions in Polar Aprotic Solvents

Kinetic data for the electroreduction of nitromesitylene at mercury in propylene carbonate have been determined in the presence of tetraalkylammonium salts of varying chain length, both as a function of electrode potential and temperature.Although the standard rate constant decreases with increase in cation size, the experimental activation enthalpy is independent of the cation for variation in this ion from tetraethylammonium to tetraoctylammonium.These results indicate that the tetraalkylammonium ions are adsorbed on the electrode forming a blocking layer whose thickness increases with alkyl chain length.Electron transfer to the redox center takes place by tunneling through this film.Theoretical estimates of the activation enthalpy support this conclusion and suggest that the redox reaction occurs in a region where solvent reorganization determines the largest portion of its magnitude.

Determination of the [15N]-nitrate/[14N]-nitrate ratio in plant feeding studies by GC–MS

Feeding experiments with stable isotopes are helpful tools for investigation of metabolic fluxes and biochemical pathways. For assessing nitrogen metabolism, the heavier nitrogen isotope, [15N], has been frequently used. In plants, it is usually applied in form of [15N]-nitrate, which is assimilated mainly in leaves. Thus, methods for quantification of the [15N]-nitrate/[14N]-nitrate ratio in leaves are useful for the planning and evaluation of feeding and pulse–chase experiments. Here we describe a simple and sensitive method for determining the [15N]-nitrate to [14N]-nitrate ratio in leaves. Leaf discs (8 mm diameter, approximately 10 mg fresh weight) were sufficient for analysis, allowing a single leaf to be sampled multiple times. Nitrate was extracted with hot water and derivatized with mesitylene in the presence of sulfuric acid to nitromesitylene. The derivatization product was analyzed by gas chromatography–mass spectrometry with electron ionization. Separation of the derivatized samples required only 6 min. The method shows excellent repeatability with intraday and interday standard deviations of less than 0.9 mol%. Using the method, we show that [15N]-nitrate declines in leaves of hydroponically grown Crassocephalum crepidioides, an African orphan crop, with a biological half-life of 4.5 days after transfer to medium containing [14N]-nitrate as the sole nitrogen source.

Selective Mild Oxidation of Anilines into Nitroarenes by Catalytic Activation of Mesoporous Frameworks Linked with Gold-Loaded Mn3O4 Nanoparticles

This work reports the synthesis and catalytic application of mesoporous Au-loaded Mn3O4 nanoparticle assemblies (MNAs) with different Au contents, i. e., 0.2, 0.5 and 1 wt %, towards the selective oxidation of anilines into the corresponding nitroarenes. Among common oxidants, as well as several supported gold nanoparticle platforms, Au/Mn3O4 MNAs containing 0.5 wt % Au with an average particle size of 3–4 nm show the best catalytic performance in the presence of tert-butyl hydroperoxide (TBHP) as a mild oxidant. In all cases, the corresponding nitroarenes were isolated in high to excellent yields (85–97 %) and selectivity (>98 %) from acetonitrile or greener solvents, such as ethyl acetate, after simple flash chromatography purification. The 0.5 % Au/Mn3O4 catalyst can be isolated and reused four times without a significant loss of its activity and can be applied successfully to a lab-scale reaction of p-toluidine (1 mmol) leading to the p-nitrotulene in 83 % yield. The presence of AuNPs on the Mn3O4 surface enhances the catalytic activity for the formation of the desired nitroarene. A reasonable mechanism was proposed including the plausible formation of two intermediates, the corresponding N-aryl hydroxylamine and the nitrosoarene.

Method and device for preparing methylnitro-benzene by channelization

The invention discloses a method and a device for preparing methylnitro-benzene by channelization. The device comprises a storage tank, a nitrogen dioxide cylinder, an ozone generator, a flow pump, agas flowmeter, a reaction pipeline filled with a catalyst, a mixing pipeline, two T-shaped mixed joints, a cooling system, a heating system, a back pressure valve and a receiving tank. The method specifically comprises the following steps: opening the cooling system and the heating system; opening the ozone generator; arranging the flow pump and the gas flowmeter; and mixing raw materials liquid methyl benzene and nitrogen dioxide through the first T-shaped mixing joint and feeding the mixture into the mixing pipeline, then mixing the mixture with ozone in the second T-shaped mixing joint, feeding the mixture into the reaction pipeline filled with the catalyst for a nitrifying reaction, and post-treating a reaction liquid to obtain methylnitro-benzene. The method is controlled precisely and automatically, and is simple to operate, mild in reaction condition, simple in post treatment, quick to transfer mass and heat, high in safety and good in economical benefit.

HNO3/HFIP: A Nitrating System for Arenes with Direct Observation of π-Complex Intermediates

This report describes an efficient nitrating system for the nitration of arenes at room temperature by using an equivalent of nitric acid in HFIP (1,1,1,3,3,3-hexafluoroisopropanol). The π-complex intermediate of an arene with a nitronium ion stabilized by HFIP can be directly observed by UV-vis spectra and is supported by theoretical calculations.

POLYCYCLIC AMINES AS OPIOID RECEPTOR MODULATORS

The present invention provides a genus of polycyclic amines that are useful as opioid receptor modulators. The compounds of the invention are useful in both therapeutic and diagnostic methods, including for treating pain, neurological disorders, cardiac disorders, bowel disorders, drug and alcohol addiction, drug overdose, urinary disorders, respiratory disorders, sexual dysfunction, psoriasis, graft rejection or cancer.

NH4I/tert-butyl hydroperoxide-promoted oxidative C–N cleavage of tertiary amines leading to nitroaromatic compounds

A NH4I/tert-butyl hydroperoxide-promoted oxidation of tertiary N-aryl-N,N-dialkylamines in DMSO has been developed to access nitroaromatic compounds. This methodology involves sequential N-dealkylation reactions in one-pot and a radical pathway is proposed.

Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite

An efficient protocol for the nitration of aromatic compounds in the presence of a catalytic amount of sulfuric acid-functionalized silica-based magnetic core/shell nanocomposite was reported. The designed products were obtained in high yields in relatively short reaction times at room temperature under solvent-free conditions. The nanocatalyst was simply recovered from the reaction mixture by using an external magnet and efficiently reused for several times. The characterization of particle size, morphology and elemental analysis of the nanocatalyst were provided by scanning electron microscopy, transmission electron microscopy and energy-dispersive X-ray spectroscopy analyses, respectively.

One-Pot C?H Functionalization of Arenes by Diaryliodonium Salts

A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.

Chemoselective reduction and self-immolation based FRET probes for detecting hydrogen sulfide in solution and in cells

Hydrogen sulfide (H2S) has been regarded as the third gaseous transmitter. Based on the mechanism of chemoselective azido reduction and self-immolation, five fluorescence resonance energy transfer (FRET) probes for the detection of H2S were designed and synthesized. The effect of functional substitution of the self-immolative moiety on azido reduction and quinone-methide rearrangement were investigated. Their fluorescence responses and chemoselectivity for H2S detection were evaluated in solutions and in cells. This strategy may provide a general route for designing H 2S probes with many commercially available FRET pairs. the Partner Organisations 2014.