67083-28-7

Usage

Uses

Used in Dye and Pigment Production:
3-Nitro-2,6-xylidine is used as a key intermediate in the production of various dyes and pigments, contributing to the coloration and stability of these substances in different applications.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3-Nitro-2,6-xylidine is employed as a crucial intermediate for the synthesis of various medicinal compounds, playing a significant role in the development of new drugs.
Used in Agrochemical Production:
3-Nitro-2,6-xylidine also serves as an intermediate in the synthesis of agrochemicals, aiding in the creation of products that protect crops and enhance agricultural productivity.

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

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 7664-93-9 sulfuric acid 
• 16939-27-8 N-(2,6-dimethylphenyl)-benzene sulfonamide 
• 143032-15-9 1,7-Dimethyl-4-nitro-1,3-dihydro-benzo[c]isothiazole 2,2-dioxide 
• 5416-12-6 N-(2,6-dimethyl-3-nitro-phenyl)acetamide 
• 855227-16-6 benzenesulfonic acid-(2,6-dimethyl-3-nitro-anilide) 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 

Downstream Products

• 35113-96-3 2-chloro-1,3-dimethyl-4-nitrobenzene 
• 603-02-1 2,4-dinitro-m-xylene 
• 60956-25-4 2-bromo-1,3-dimethyl-4-nitrobenzene 
• 6994-63-4 2,6-dimethyl-3-nitro-phenol 
• 4102-46-9 2-iodo-1,3-dimethyl-4-nitrobenzene 
• 69383-57-9 4-Nitro-1.3-dimethyl-benzol-2-sulfonylchlorid 
• 855227-16-6 benzenesulfonic acid-(2,6-dimethyl-3-nitro-anilide) 
• 39189-62-3 2-(2,6-Dimethyl-3-nitro-phenylamino)-benzoic acid 
• 133053-69-7 methyl N-(2,6-dimethyl-3-nitrophenyl)-formimidate 
• 50536-74-8 2,6-dimethyl-3-nitroanisole 
• 295325-86-9 4-methoxy-5-methylindole 
• 295325-87-0 4-methoxy-5-methylindoline 
• 10553-07-8 7-methyl-4-nitro-1H-indole 
• 133053-70-0 7-methyl-6-nitroindole 

Relevant academic research and scientific papers

Conformational control of bis-urea self-assembled supramolecular pH switchable low-molecular-weight hydrogelators

We report the synthesis and investigation into the structure-property relationships of eight different low molecular weight hydrogelators based on a bisaromatic urea core unit, all of which form gels as the pH of the solution is lowered. The low molecular weight hydrogelators are functionalized with carboxylic acid moieties on one aromatic ring, and the other aromatic ring features a nitro functional group either in the meta- or paraposition relative to the urea linkage. Ortho-methyl substituents were installed on the aromatic rings to enforce a non-coplanar arrangement between the phenyl and urea moieties. Gel formation was triggered by the addition of a mineral acid or the ring-opening hydrolysis of glucono-δ-lactone. The low molecular weight hydrogelators were studied by a variety of analytical techniques, including NMR spectroscopy and rheology. In addition, their ability to uptake a dye, methylene blue, was determined by UV-vis spectroscopy. (Figure Presented)

Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis

An efficient oxidative NHC-catalyzed one-step transformation of (S)-or (R)-8-oxocitronellal to nepetalactone (NL) in enantio- A nd diastereomerically pure form has been developed. Several new and "easy to make" N-Mes-or N-Dipp-substituted 1,2,4-triazolium salts carrying nitroaromatic groups on N1 were synthesized and evaluated as precatalysts in combination with base and stoichiometric organic oxidant. Under optimized conditions, NLs are accessible in very good yields and diastereomerically pure under mild conditions. The oxidant used could be recovered and recycled under operationally simple conditions.

Cell-Based Optimization of Covalent Reversible Ketoamide Inhibitors Bridging the Unprimed to the Primed Site of the Proteasome β5 Subunit

The ubiquitin-proteasome system (UPS) is an established therapeutic target for approved drugs to treat selected hematologic malignancies. While drug discovery targeting the UPS focuses on irreversibly binding epoxyketones and slowly-reversibly binding boronates, optimization of novel covalent-reversibly binding warheads remains largely unattended. We previously reported α-ketoamides to be a promising reversible lead motif, yet the cytotoxic activity required further optimization. This work focuses on the lead optimization of phenoxy-substituted α-ketoamides combining the structure-activity relationships from the primed and the non-primed site of the proteasome β5 subunit. Our optimization strategy is accompanied by molecular modeling, suggesting occupation of P1′ by a 3-phenoxy group to increase β5 inhibition and cytotoxic activity in leukemia cell lines. Key compounds were further profiled for time-dependent inhibition of cellular substrate conversion. Furthermore, the α-ketoamide lead structure 27 does not affect escape response behavior in Danio rerio embryos, in contrast to bortezomib, which suggests increased target specificity.

Discovery of a Chemical Probe Bisamide (CCT251236): An Orally Bioavailable Efficacious Pirin Ligand from a Heat Shock Transcription Factor 1 (HSF1) Phenotypic Screen

Phenotypic screens, which focus on measuring and quantifying discrete cellular changes rather than affinity for individual recombinant proteins, have recently attracted renewed interest as an efficient strategy for drug discovery. In this article, we describe the discovery of a new chemical probe, bisamide (CCT251236), identified using an unbiased phenotypic screen to detect inhibitors of the HSF1 stress pathway. The chemical probe is orally bioavailable and displays efficacy in a human ovarian carcinoma xenograft model. By developing cell-based SAR and using chemical proteomics, we identified pirin as a high affinity molecular target, which was confirmed by SPR and crystallography.

RAF INHIBITOR COMPOUNDS AND METHODS OF USE THEREOF

Compounds of Formulas (I), (IIA) and (IIIA) are useful for inhibiting Raf kinase and for treating disorders mediated thereby. Methods of using compounds of Formulas (I), (IIA) and (IIIA) and stereoisomers and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

NOVEL 6-5 BICYCIC HETEROCYCLIC DERIVATIVE AND MEDICAL USE THEREOF

An object of the present invention is to provide a medicament as a thyroid hormone receptor ligand which is sufficient in drug efficacy and safety, and has the excellent action as a drug. The present invention provides a compound represented by the following general formula (I) or a pharmaceutically acceptable salt thereof: [wherein [Chemical Formula 2] is a single bond or a double bond; A is -CH2- or -CO-; X, Y, and Z are each independently a nitrogen atom or a carbon atom; R1 is a hydrogen atom or an aralkyl group; R2 is an alkyl group or an aralkyl group, etc.; R3 is a hydrogen atom or an alkyl group, etc.; R4 is a hydrogen atom or an alkyl group; R5 is a hydrogen atom, an alkyl group or a halo lower alkyl group, etc.; R6 is a hydrogen atom or an alkyl group; R7 is a hydrogen atom, etc.; R8 is a hydrogen atom, or an alkyl group, etc.; and E is -NHCO-G-COR12, etc. (wherein G is a single bond or an alkylene group, and R12 is a hydroxy group or an alkoxy group)].

HEPATITIS C INHIBITOR COMPOUNDS

Compounds of formula (I): wherein B, X, R3, L0, L1, L2, R2, R1 and RC are defined herein. The compounds are useful as inhibitors of HCV NS3 protease for the treatment of hepatitis C viral infection.

Reactions of aza-ortho-xylylenes generated from 2,1-benzisothiazoline 2,2-dioxides

Thermal extrusion of SO2 from 2,1-benzisothiazoline 2,2-dioxides 2 leads to aza-ortho-xylylenes 3, which depending on the substituents undergo various transformations. Aza-ortho-xylylenes substituted at the position 4, 5, and 6 gave Diels-Alder reactions with maleic acid derivatives 4 leading to cis-1,2,3,4-tetrahydroquinoline 2,3-dicarboxylic acid derivatives 5 in high yields. 7-Substituted derivatives underwent [1,5] hydrogen shift leading to ortho-toluidine derivatives 9 and 10. Aza-ortho-xylylenes generated from N-(4-pentenyl) and N-(5-hexenyl) derivatives 11 gave products of intramolecular Diels-Alder reaction.

Synthesis of Indoles via Ring Closure of 2-Alkylnitroaniline Derivatives.

A variety of nitroindoles have been prepared from imidate, amidine, and sec-anilide derivatives of 2-alkyl-3- or 5-nitroanilines by a base-induced cyclization promoted by dialkyl oxalates.It is shown that essentially the same procedure also can be used to synthesize the corresponding nitroindole-3-glyoxylates in one simple operation.The synthetic potential is discussed and a mechanism is proposed.

Revisitation of Formaldehyde Aniline Condensation. VIII. - Monomeric N-Methylene Anilines

A convenient, high yield "dry" method of synthesis of monomeric N-methyleneanilines (6a-i) and the characterization of the products by m.s., 1H- and 13C-n.m.r. and i.r. are reported, improving previous procedures and describing new compounds.It appeared that the existence of monomeric N-methyleneanilines is stricly related to the presence of enough steric hindrance to oligomerization by substituents in ortho positions.Moreover, some addition products of formaldehyde to an amine and its corresponding imines are tentatively identified on the basis of the observed mass spectrum of the whole reaction mixture.The reaction products of formaldehyde with 2,6-dimethylaniline (1a) provided an example of a mobile equilibrium between monomeric and trimeric imine.