1123-49-5

Basic information

• Product Name: 3,5-DIMETHYL-4-NITROISOXAZOLE
• Synonyms: AKOS B022232;3,5-DIMETHYL-4-NITROISOXAZOLE;ART-CHEM-BB B022232;3,5-DIMETHYL-4-NITROISOXAZOLE 98%;3,5-Dimethyl-4-nitroisoxazole ,98%;4-nitro-3,5-diMethylisoxazole;Isoxazole, 3,5-dimethyl-4-nitro-
• CAS NO: 1123-49-5
• Molecular Formula: C₅H₆N₂O₃
• Molecular Weight: 142.11
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Isoxazoles
• Mol File: 1123-49-5.mol

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 241.4℃
• Flash Point: 99.8℃
• Appearance: /
• Density: 1.293
• Vapor Pressure: 0.0559mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -3.68±0.28(Predicted)
• CAS DataBase Reference: 3,5-DIMETHYL-4-NITROISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYL-4-NITROISOXAZOLE(1123-49-5)
• EPA Substance Registry System: 3,5-DIMETHYL-4-NITROISOXAZOLE(1123-49-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1123-49-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dimethyl-4-nitroisoxazole is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows it to be incorporated into a wide range of drug molecules, making it a valuable tool in the development of new medications.
Used in Organic Synthesis:
3,5-Dimethyl-4-nitroisoxazole is used as a key building block in the synthesis of a variety of organic compounds, including methylene bis-isoxazolo[4,5-b]azepines, phenylmethylene bis-isoxazolo[4,5-b]azepine derivatives, 3-arylglutaric acids, bis-isoxazoles, and bis-pyrazoles. Its versatility in chemical reactions makes it an important component in the synthesis of complex organic molecules.
Used in Research and Development:
3,5-Dimethyl-4-nitroisoxazole is used as a research compound in the development of new synthetic methods and the study of chemical reactions. Its unique properties and reactivity make it an interesting subject for research in the field of organic chemistry.

InChI:InChI=1/C5H6N2O3/c1-3-5(7(8)9)4(2)10-6-3/h1-2H3

Upstream product

• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 186581-53-3 diazomethane 
• 1122-05-0 3-methyl-4-nitroisoxazole 
• 108560-92-5 (Z)-3,5-dimethyl-5-hydroxi-4-hydroxyimino-2-isoxazoline 
• 29917-12-2 Isonitrosoacetylacetone 
• 123-54-6 acetylacetone 
• 16990-73-1 2-Hydroxyindole 
• 132712-71-1 5-hydroxy-3-methylpyrazole 
• 2295-31-0 thiazoline-2,4-dione 
• 4303-29-1 4-thioxo-2-thiazolidinone 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 75-52-5 nitromethane 
• 109-77-3 malononitrile 
• 603-76-9 1-methylindole 

Downstream Products

• 53557-96-3 3-methyl-4-nitro-5-(4t-phenyl-buta-1,3-dien-t-yl)-isoxazole 
• 90008-59-6 4-Nitro-3,5-dimethyl-1-ethylpyrazol 
• 51978-94-0 (E)-3-methyl-4-nitro-5-styrylisoxazole 
• 51978-98-4 5-[(E)-2-(4-methoxyphenyl)-1-ethenyl]-3-methyl-4-nitroisoxazole 
• 5809-38-1 3,5-dimethyl-4-nitro-1-phenyl-1H-pyrazole 
• 53557-99-6 N,N-dimethyl-4-[trans-2-(3-methyl-4-nitro-isoxazol-5-yl)-vinyl]-aniline 
• 31329-64-3 3,5-dimethylisoxazol-4-amine 
• 14531-55-6 3,5-dimethyl-4-nitro-1H-pyrazole 
• 68257-76-1 3-(4-chloro-phenyl)-4-(3-methyl-4-nitro-isoxazol-5-yl)-1-phenyl-butan-1-one 
• 68257-77-2 3-(4-chloro-phenyl)-4-(3-methyl-4-nitro-isoxazol-5-yl)-1-p-tolyl-butan-1-one 
• 68257-73-8 4-(3-methyl-4-nitro-isoxazol-5-yl)-1-naphthalen-2-yl-3-phenyl-butan-1-one 
• 68257-78-3 3-(2,4-dichloro-phenyl)-4-(3-methyl-4-nitro-isoxazol-5-yl)-1-phenyl-butan-1-one 
• 91975-03-0 4-Nitro-3-methyl-5-<2-(4-nitro-anilino)-vinyl>-isoxazol 
• 68257-70-5 3-methyl-4-nitro-5-(2,4-diphenyl-4-oxobutyl)isoxazole 

Relevant articles and documents

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium

The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used

Styrylisoxazole-based fluorescent probes for the detection of hydrogen sulfide

Styrylisoxazoles bearing a nitro group linked to bulky aromatic rings have been synthesized and examined for their absorption and emission studies in organic solvents and water. The molecules showed emission in the visible region with significant solvatochromic emission shifts influenced by the extended conjugation of aromatic rings and intramolecular charge transfer. These absorption and emission changes were used for the efficient and sensitive detection of trace concentrations of hydrogen sulfide (H2S) through the reduction of the nitro group to the amine group in the presence of aqueous sodium sulfide. The experimental results indicated that the probes exhibit an excellent emission response with large shifts in the emission and sensitivity with a micromolar detection limit.

Development and Scale-up of an Organocatalytic Enantioselective Process to Manufacture (S)-Pregabalin

Herein is reported the development of a new process to manufacture (S)-pregabalin. The method comprises six steps, run under the catalysis of a recyclable polymer bound phase transfer catalyst, and afforded (S)-pregabalin in overall 54% yield, starting from building blocks acetylacetone, isovaleraldehyde, and nitromethane.

Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

Highly efficient asymmetric vinylogous 1,6-Michael addition of α,β-unsaturated γ-butyrolactam to 3-methyl-4-nitro-5-alkenyl- isoxazoles and Michael addition to trichloromethyl ketones by using a chiral quinine-derived squaramide organocatalyst were described, giving products with high diastereo- and enantioselectivities (up to >25:1 dr and 96% ee).

Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride, including selected microwave examples

A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved resulting in the synthesis of several novel organic compounds. A distinct advantage is the removal of undesired byproducts by aqueous workup. This very mild nitration permits large-scale syntheses and gives high isolated product yields that often require no further purification. This tetramethylammonium nitrate-based nitration also has been applied to microwave-assisted conditions, and the results with several compounds are outlined.

DIRECT FIVE-MEMBERED HETEROANNULATION REACTIONS FOR THE ISOXAZOLE SYSTEM BY 1,3-DIPOLAR CYCLOADDITIONS ON 5-UNSUBSTITUTED 4-NITRO DERIVATIVES: SYNTHESIS OF PYRAZOLO- AND PYRROLOISOXAZOLES

One-step syntheses of aromatic derivatives of the title binuclear systems have been achieved by reaction of compound 3b with diazomethane, as well as by treatment of 3a and 3b with diphenylnitrilimine and 3-methyl-2,4-diphenyloxazolium 5-oxide, respective

Transformations in the isoxazole series: Synthesis of substituted 2-aminothiazoles

Substitued N-(isoxazol-4-yl)thioureas 1 undergo a transformation in the presence of hexacarbonylmolybdenum and acid to yield functionalized thiazoles 3 in a one-pot reaction. In a few cases, 1,4,5-trisubstituted dihydroimidazoleth, iones 4 are also isolated as side products. Mechanistic considerations are outlined and scope and limitations of this new methodology discussed.

Flash Vacuum Pyrolysis of Some 4-Nitroisoxasoles

Flash vacuum pyrolysis (FVP) of some 5-alkyl-3-methyl-4-nitroisoxasoles affords 1-nitro-1-cyanoacetone as the only product.A general mechanism is suggested which involves isomerization of the isoxazole to a 1-azirine.A nonclassical reaction of 3-methyl-4-nitroisoxazoles is assumed as a consequence of the electron-withdrawing ability of the nitro group, which precludes ring closure of the nitrile ylide intermediate to the oxazole isomer.The formation of 1-nitro-1-cyanoacetone by FVP of the 3-unsubstituted 5-methyl-4-nitroisoxazole suggests that the activation barrier for a 1,2-hydrogen shift from a 1-azirine or vinylnitrene is lower than that for the formation of nitrile ylide.The FVP of 5-ethyl-3-methylisoxzaole affords 5-ethyl-2-methyloxazole.

Oximation of Acetyl(hydroxyimino)aceton: Nuclear Magnetic Resonance Spectroscopic, Chemical, and X-Ray Crystallographic Studies of the Reaction Products

The oximation of acetyl(hydroxyimino)aceton (1) with hydroxylamine affords a mixture of oxime derivatives.The products obtained by the action of an equimolar amount of hydroxylamine on (1) are the two 3,5-dimethyl-5-hydroxy-4-hydroxyimino-2-isoxazoline isomers (3a and b).The main products obtained by the action of an excess of hydroxylamine on (1) are two pentane-2,3,4-trione trioxime isomers (4a and b) and a little amount of 4-acetyl-3-methylfuroxan oxime (5).N.m.r. and chemical data of all these derivatives are discussed in order to determine both structures and configuration.X-Ray analysis of (3a), (4a), and (5) are also reported.