1635-84-3

Usage

Uses

Used in Pharmaceutical Industry:
4,6-DIMETHYL-2-NITROANILINE is used as a reagent for the synthetic preparation of 1,2-bis-substituted benzimidazoles, which are nonnucleoside HIV-1 reverse transcriptase inhibitors. These inhibitors play a crucial role in the development of antiretroviral drugs, as they help in the treatment of HIV and AIDS by blocking the replication of the virus.
In the synthesis process, 4,6-DIMETHYL-2-NITROANILINE serves as a key intermediate, providing the necessary structural features required for the formation of the final benzimidazole product. The compound's reactivity and functional groups enable it to undergo various chemical reactions, such as nucleophilic substitution, electrophilic aromatic substitution, and reduction, which are essential for the synthesis of the desired benzimidazole derivatives.
The development of nonnucleoside HIV-1 reverse transcriptase inhibitors is of great importance in the fight against HIV and AIDS, as these drugs offer an alternative treatment option for patients who may not respond well to or cannot tolerate other antiretroviral medications. By using 4,6-DIMETHYL-2-NITROANILINE as a reagent in the synthesis of these inhibitors, researchers can explore new chemical structures and potentially discover more effective and safer drugs to combat the virus.

InChI:InChI=1/C8H10N2O2/c1-5-3-6(2)8(9)7(4-5)10(11)12/h3-4H,9H2,1-2H3

Upstream product

• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 593255-20-0 2-iodo-3,5-dimethyl-1-nitrobenzene 
• 200123-90-6 N-(2,4-dimethylphenyl)methanesulfonamide 
• 95-68-1 2,4-Xylidine 
• 685568-79-0 N-(2,4-dimethyl-6-nitrophenyl)methanesulfonamide 
• 7664-93-9 sulfuric acid 
• 90223-39-5 2,4-dimethyl-6,N-dinitro-aniline 
• 64-19-7 acetic acid 
• 65151-56-6 3,5-dimethyl-1,2-dinitrobenzene 
• 7664-41-7 ammonia 
• 606-38-2 N-(2,4-dimethyl-6-nitro-phenyl)-acetamide 
• 25116-90-9 N-(2,4-dimethylphenyl)benzenesulfonamide 

Downstream Products

• 327619-41-0 N-(2,6-difluorobenzoyl)-2,4-dimethyl-6-nitroaniline 
• 2803-23-8 N,O-bis-(1-cyano-1-methyl-ethyl)-N-(2-fluoro-3,5-dimethyl-phenyl)-hydroxylamine 
• 60190-73-0 C₂₆H₂₅N₂P 
• 60190-75-2 C₄₄H₃₈N₂P₂ 
• 939018-67-4 N₂-(2,4-dimethyl-6-nitrophenyl)-N₁,N₁-dimethylglycinamide 
• 862307-78-6 2,6-dimethyl-2-nitrophenyl azide 
• 183492-49-1 4,6-dimethyl-2-nitrotrifluoroacetanilide 
• 593255-20-0 2-iodo-3,5-dimethyl-1-nitrobenzene 
• 64835-42-3 4,6-dimethyl-2-nitrobenzenesulfonyl chloride 
• 35490-76-7 2-bromo-3,5-dimethylphenylamine 
• 58579-99-0 2,4-dimethyl-6-nitro-benzonitrile 
• 110513-06-9 toluene-4-sulfonic acid-(2,4-dimethyl-6-nitro-anilide) 
• 3171-46-8 3,5-dimethylbenzene-1,2-diamine 
• 140646-97-5 1,5-dimethyl-3-nitro-2-nitroso-benzene 

Relevant academic research and scientific papers

Indole and indazole compounds as an inhibitor of cellular necrosis

The present invention refers to a formula (1) compounds of, pharmaceutically acceptable salts or isomers thereof thereof, and characterized by by containing as active ingredients-associated diseases, cell death and method for the prevention or treatment of relates and compositions. [Formula 1] In formula said R 1, R 2, R 3, R 4, R 5, R 6, A, X, n and m to equal the specification.

First demonstration of positive allosteric-like modulation at the human wild type translocator protein (TSPO)

We show that changing the number and position of nitrogen atoms in the heteroatomic core of a pyrazolopyrimidine acetamide is sufficient to induce complex binding to wild type human TSPO. Only compounds with this complex binding profile lacked intrinsic effect on glioblastoma proliferation but positively modulated the antiproliferative effects of a synthetic TSPO ligand. To the best of our knowledge this is the first demonstration of allosteric-like interaction at the wild type human TSPO.

Green recyclable CuO-CeO2 nanocomposite catalyzed amination of aryl halides with aqueous ammonia in water

CuO-CeO2 nanocomposite as a green recyclable catalyst, catalyzed amination of aryl halides with aqueous ammonia in water. This catalyst can be easily recovered by simple filtration and recycled up to 5 consecutive runs with consistent activity. The procedure provides some advantages such as simple work-up, clean procedure, relatively short reaction times and high yields of the products. Efficient procedure for the amination of aryl halides catalyzed by Cu-CeO2 nanocomposite. Copyright

INDOLE AND INDAZOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS

The present invention relates to indole or indazole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole or indazole compounds as an active ingredient.

INDOLE AND INDAZOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS

The present invention relates to indole or indazole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole or indazole compounds as an active ingredient.

Nitration and Bromination of N-(dimethylphenyl)methanesulfonamides

The orientation of the products of nitrosation: nitration and bromination of the methanesulfonamides of the six isomeric dimethylanilines have been established by 1H NMR nuclear Overhauser experiments.

Syntheses and resolutions of new chiral biphenyl backbones: 2-Amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′- biphenyl

The new chiral backbones (R)-(+)- and S-(-)-2-amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and (R)-(+)- and (S)-(-)-2-amino-2′-hydroxy-4,4′,6,6′- tetramethyl-1,1′-biphenyl were synthesized from o-methylaniline and 2,4-dimethyl-aniline respectively in seven steps. A new resolution method was developed to provide homochiral enantiomers (from diastereomeric salts) in reasonably high yields. The absolute configuration of the new biphenyls was confirmed by X-ray structural analysis.

Direct Nitration of Anilines Using Nitrocyclohexadienones

Nitrocyclohexadienones (in particular, 2,3,5,6-tetrabromo-4-methyl-4-nitro-2,5-cyclohexadienone) are used as reagents for the direct nitration of anilines.Depending on the conditions, good yields of C-nitroanilines are obtained.Under the same conditions, N,N-dimethylaniline is converted into N-methyl-N-nitroaniline.

Axially Dissymmetric Bis(triaryl)phosphines in the Biphenyl Series: Synthesis of (6,6'-Dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh(I)-Catalyzed Asymmetric Isomerisations of N,N-Diethylnerylamine

The axially dissymmetric diphosphines (-)-(R)- and (+)-(S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)((-)-(R)-10 and (+)-(S)-10; 'BIPHEMP') have been synthesized, starting from (R)- and (S)-6,6'-dimethylbiphenyl-2,2'-diamine ((R)- and (S)-16), respectively, via Sandmeyer reaction, lithiation, and phosphinylation.Moreover, racemic 4,4'-dimethyl- and 4,4'-bis(dimethylamino)-substituted analogues 11 and 12, respsctively, and the 6,6'-bridged analogue 1,11-bis(diphenylphosphino)-5,7-dihydrodibenzoxepin (13) were synthesized and resolved into optically pure (R)- and (S)-enantiomers via complexation with di-μ-chlorobisphenyl-C,N>dipalladium(II) ((R)-18).The molecular structures of the diphosphines (S)-10 and (R)-13 and of two derived cationic Rh(I) complexes, BF4 and BF4 were determined by X-ray analyses.Absolute configurations were established for (+)-(S)-10 by X-ray analyses of both the free diphosphine and of the derived Rh(I) complex, and for (-)-13 by X-ray analysis of the derived Rh(I) complex.Configurational assignments for the substituted BIPHEMP analogues 11 and 12 were achieved by means of 1H-NMR comparisons of the Pd(II) complexes derived from the diphosphines and (R)-18, and by means of CD comparisons.The BIPHEMP ligand 10 and analogues 11, 12, and 13 are the first examples of optically active bis(triarylphosphines) containing the axially dissymmetric biphenyl moiety.All these new diphosphines proved to be excellent asymmetry-inducing ligands in Rh(I)-catalyzed isomerizations of N,N-diethylnerylamine affording citronellal enamine of 98-99percent ee.

Studies of Reactions of Amines with Sulfur Trioxide. VI. Thermal Reactions of Anilinium, Dimethylanilinium, and Trimethylanilinium Salts of Butylamidosulfuric Acid

When the title compounds were heated in an evacuated reaction vessel, both transsulfonation and rearrangement occurred.At lower temperatures (80-120 deg C) the corresponding phenylamidosulfates and sulfophenylamidosulfates (transsulfonation products) were the main products.Increasing temperature led to the formation of ring mono- and disulfonates (rearrangement products) at the expense of the transsulfonation products.The sulfonate group always migrated to the ortho and/or para position(s) to the amino group.In no case was any meta-product detected.There was no significant difference in the ease of transsulfonation among the anilinium salts studied exept 2,6-dimethyl- and 2,4,6-trimethylanilinium salts.On the other hand, the ease of rearrangement and the orientation of ring sulfonation depended strongly on the structure of the substrate anilines.The thermal reactions of 2,4,6-trimethylanilinium butylamidosulfate produced (2,4,6-trimethylphenylimido)bis(sulfate) in addition to (2,4,6-trimethylphenylamido)sulfate.This is the first isolation of an arylimidobis(sulfate) from such reactions.Mechanisms of the transsulfonation and rearrangement have been discussed.