14804-39-8

Usage

Uses

Used in Chemical Synthesis:
2,6-Dimethyl-4-nitroanisole is used as a chemical intermediate for the synthesis of various compounds, particularly in the production of dyes. Its reactivity, due to the presence of the nitro group and the methyl groups, makes it a valuable component in the creation of a wide range of chemical products.
Used in Dye Production:
In the dye industry, 2,6-Dimethyl-4-nitroanisole is used as a key component in the synthesis of dyes. Its chemical properties allow for the development of a variety of colorants that can be used in different applications, such as textiles, plastics, and printing inks.
Used in Pharmaceutical Industry:
2,6-Dimethyl-4-nitroanisole is also used as a building block in the synthesis of certain pharmaceutical compounds. Its reactivity and structural features make it a useful precursor for the development of new drugs and medicinal agents.
Used in Research and Development:
Due to its unique chemical properties, 2,6-Dimethyl-4-nitroanisole is utilized in research and development settings to explore new chemical reactions and pathways. It serves as a model compound for understanding the behavior of similar organic compounds and their potential applications in various fields.
However, it is important to note that the use of 2,6-Dimethyl-4-nitroanisole comes with certain risks. Its potential for explosiveness under specific conditions and possible health risks associated with exposure must be carefully managed to ensure safety in its handling and application.

InChI:InChI=1/C9H11NO3/c1-6-4-8(10(11)12)5-7(2)9(6)13-3/h4-5H,1-3H3

Upstream product

• 1004-66-6 2-methoxy-1,3-dimethylbenzene 
• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 
• 2423-71-4 2,6-dimethyl-4-nitro phenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 55215-54-8 5-iodo-2-methoxy-1,3-dimethylbenzene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 16947-63-0 2,6-dimethyl-4-nitroaniline 
• 5399-03-1 2-iodo-1-methoxy-4-nitrobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 512-56-1 trimethyl phosphite 
• 576-26-1 2.6-dimethylphenol 
• 39785-37-0 4-amino-2,6-dimethylanisole 

Downstream Products

• 2423-71-4 2,6-dimethyl-4-nitro phenol 
• 39785-37-0 4-amino-2,6-dimethylanisole 
• 23019-47-8 N-acetyl-4-methoxy-3,5-dimethylaniline 
• 854854-83-4 4-methoxy-3,5-dimethyl-2-nitro-aniline 
• 860580-43-4 acetic acid-(4-methoxy-2-nitro-3,5-dimethyl-anilide) 
• 1170949-96-8 4-acetamido-2,6-dimethyl-5-iodoanisole 
• 1170949-99-1 4-acetamido-2,6-dimethyl-5-iodo-3-nitroanisole 
• 1170950-07-8 (±)-4-acetamido-2,6-dimethyl-5-[3’,4’-dihydroxy-3’-methylbut-1’-yn-1’-yl]-3-nitroanisole 
• 1170950-10-3 (±)-4-acetamido-3-amino-2,6-dimethyl-5-[3’,4’-dihydroxy-3’-methylbut-1’-yl]anisole 
• 948018-43-7 (R)-N-(3,5-dimethyl-4-methoxyphenyl)-(1-(4-chlorophenyl)ethyl)amine 

Relevant academic research and scientific papers

Medium-Sized Cyclophanes. 43. First Evidence for anti-syn-Ring Inversion under the Nitration of 5,13-Di-tert-butyl-8,16-dimethoxy[2.2]metacyclophane

Nitration of 5,13-di-tert-butyl-8,16-dimethoxy[2.2]MCP (metacyclophane = MCP) (1) with various nitrating reagents led to ipso-nitration at the tert-butyl group to give 5-tert-butyl-8,16-dimethoxy-13-nitro[2.2]MCP (2), as well as the corresponding 8,16-epo

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

N-Heterocyclic Carbene-Catalyzed Truce-Smiles Rearrangement of N-Arylacrylamides via the Cleavage of Unactivated C(aryl)-N Bonds

We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Synthesis of a poly-heterocyclic tetra-substituted alkene via a palladium-catalyzed four-fold domino reaction for the design of polymeric molecular switches

A facile synthesis of a complex poly-heterocyclic tetrasubstituted alkene 4 with intrinsic helical chirality containing two acrylate moieties suitable for polymerization is described. Compound 4 can act as a molecular switch and was prepared via a palladi

Palladium-Catalyzed 4-Fold Domino Reaction for the Synthesis of a Polymeric Double Switch

A palladium-catalyzed 4-fold domino reaction consisting of two carbopalladation reactions and two C-H activation reactions, followed by the introduction of an acrylate moiety, led to the tetra-substituted helical alkene A2, using the dialkyne A3 as a subs

Semi-quantitative models for identifying potent and selective transthyretin amyloidogenesis inhibitors

Rate-limiting dissociation of the tetrameric protein transthyretin (TTR), followed by monomer misfolding and misassembly, appears to cause degenerative diseases in humans known as the transthyretin amyloidoses, based on human genetic, biochemical and pharmacologic evidence. Small molecules that bind to the generally unoccupied thyroxine binding pockets in the native TTR tetramer kinetically stabilize the tetramer, slowing subunit dissociation proportional to the extent that the molecules stabilize the native state over the dissociative transition state—thereby inhibiting amyloidogenesis. Herein, we use previously reported structure-activity relationship data to develop two semi-quantitative algorithms for identifying the structures of potent and selective transthyretin kinetic stabilizers/amyloidogenesis inhibitors. The viability of these prediction algorithms, in particular the more robust in silico docking model, is perhaps best validated by the clinical success of tafamidis, the first-in-class drug approved in Europe, Japan, South America, and elsewhere for treating transthyretin aggregation-associated familial amyloid polyneuropathy. Tafamidis is also being evaluated in a fully-enrolled placebo-controlled clinical trial for its efficacy against TTR cardiomyopathy. These prediction algorithms will be useful for identifying second generation TTR kinetic stabilizers, should these be needed to ameliorate the central nervous system or ophthalmologic pathology caused by TTR aggregation in organs not accessed by oral tafamidis administration.

A new tactic for tocopherol synthesis using intramolecular benzyne trapping by an alcohol

A formal total synthesis of (S)-α-Tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-Amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.

Synthesis of a new mutagenic benzoazepinoquinolinone derivative

A novel mutagenic compound 1, isolated as a Maillard product from tryptophan and glucose, was synthesized using Larock's quinoline formation, where addition of iodonium cation to an acetylene moiety of N-propargylaniline triggers subsequent intramolecular

A synthesis of α-tocopherol featuring benzyne trapping by an alcohol

A formal total synthesis of α-tocopherol, the main component of Vitamin E, has been achieved in which a central step is the intramolecular trapping of a highly substituted benzyne by an alcohol group to establish the pyran ring.