2735-04-8

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dimethoxyaniline is used as a starting material for the synthesis of various pharmaceutical compounds, specifically 2,4-dimethoxyphenylsemicarbazones. These semicarbazones have potential applications in the development of new drugs due to their diverse chemical structures and biological activities.
Used in Chemical Synthesis:
2,4-Dimethoxyaniline is used as a chemical intermediate for the production of various organic compounds. Its unique structure allows for further functionalization and modification, making it a versatile building block in the synthesis of a wide range of chemicals.
Used in Research and Development:
2,4-Dimethoxyaniline is utilized in research and development for the exploration of new chemical reactions and the development of novel synthetic methods. Its reactivity and structural features make it an interesting candidate for studying various organic transformations and reaction mechanisms.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 2441, 1993 DOI: 10.1016/S0040-4039(00)60436-7

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,4-Dimethoxyaniline neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: 2,4-Dimethoxyaniline is a local irritant.

InChI:InChI=1/C7H9NO2/c1-10-5-2-3-6(8)7(9)4-5/h2-4,9H,8H2,1H3

Upstream product

• 29418-46-0 (2,4-dimethoxy-phenyl)-phenyl-diazene 
• 4920-84-7 2,4-dimethoxynitrobenzene 
• 23042-75-3 N-(2,4-dimethoxyphenyl)acetamide 
• 4107-65-7 2,4-dimethoxybenzonitrile 
• 151-10-0 1,3-Dimethoxybenzene 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 91-23-6 2-Nitroanisole 
• 592489-17-3 1,3-dimethyl-2-(2,4-dimethoxyphenylimino)imidazolidine 
• 20629-90-7 1-(2-chlorophenyl)-3-methyl-5-pyrazolone 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 29418-55-1 bis-(2,4-dimethoxy-phenyl)-diazene 
• 133730-34-4 2,4-dimethoxyphenylboronic acid 
• 85862-79-9 1-azido-2,4-dimethoxybenzene 

Downstream Products

• 2672-82-4 2-hydroxy-dibenzofuran-3-carboxylic acid-(2,4-dimethoxy-anilide) 
• 109393-40-0 3-oxo-3-phenyl-propionic acid-(2,4-dimethoxy-anilide) 
• 349407-99-4 (3,4-dimethoxy-phenyl)-acetic acid-(2,4-dimethoxy-anilide) 
• 2876-29-1 2-Methoxy-phenazin-10-oxid 
• 101908-41-2 2-chloro-N-(2,4-dimethoxyphenyl)acetamide 
• 116557-72-3 p-toluenesulfonyl-2,4-dimethoxyaniline 
• 430454-31-2 methoxy-acetic acid-(2,4-dimethoxy-anilide) 
• 2672-77-7 3-hydroxy-[2]naphthoic acid-(2,4-dimethoxy-anilide) 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 39501-57-0 2,4-dimethoxy-1-nitrosobenzene 
• 39886-58-3 6-methyl-[1,3]oxazinane-3-carboxylic acid (2,4-dimethoxy-phenylcarbamoyl)-amide 
• 39886-68-5 C₂₄H₂₅N₃O₄ 
• 21022-18-4 N,N'-Bis-(2,4-dimethoxy-phenyl)-oxalamide 
• 29140-18-9 2-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[e][1,2]thiazine-4-carboxylic acid 2,4-dimethoxy-anilide 

Relevant academic research and scientific papers

Methoxy aniline compound and synthesis method thereof

The invention mainly relates to a preparation method of anisidine. According to the technical scheme, under the promotion of the photocatalyst and blue light, in the argon atmosphere, nitro compounds and methanol generate methoxyaniline, wherein products and additional products with stable molecular structures and excellent chemical properties are prepared, wherein a photocatalyst and a blue light source are used in the method, and a new path is provided for synthesis of methoxyaniline compounds. The method has the characteristics of mild reaction conditions, simple reaction system, less reaction equipment, simplicity and convenience in experimental operation and the like. The methoxyaniline derivative and the synthetic method thereof can be applied to a plurality of industrial production fields of dyes, pesticides, medicines, rubber additives and the like. The method is particularly suitable for scientific research, development and utilization of efficient and selective synthesis of methoxyaniline compounds by a one-pot method.

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Cu(II)-Mediated N-H and N-Alkyl Aryl Amination and Olefin Aziridination

Cu(II)-mediated direct NH2 and NH alkyl aryl aminations and olefin aziridinations are described. These room-temperature, one-pot, environmentally friendly procedures replace costly Rh2 catalysts and, in some instances, display important differences with comparable Rh2- and Fe-supported reactions.

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.

Secondary amides as hydrogen atom transfer promoters for reactions of samarium diiodide

Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives with SmI2 in THF to estimate the extent of N-H bond weakening upon coordination. Mechanistic and synthetic studies demonstrate significant bond-weakening, providing a reagent system capable of reducing a range of substrates through formal hydrogen atom transfer.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.

Transition-metal-free access to primary anilines from boronic acids and a common +NH2 equivalent

Diversely substituted anilines are prepared by treatment of functionalized arylboronic acids with a common, inexpensive source of electrophilic nitrogen (H2N-OSO3H, HSA) under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method. However, even moderately electron-poor substrates are well tolerated under the room temperature conditions. Sterically hindered substrates appear to be equally effective compared to unhindered ones. Highly electron-deficient substrates afford product in very low yields at room temperature, but moderate to good yields are obtained at refluxing temperatures. Our method is also amenable to electrophilic amination of several common boronic acid derivatives (e.g., pinacol esters). We demonstrate that it can be combined with metal-halogen exchange reactions or a variety of directed ortho metalation protocols in a "one-pot" sequence for the synthesis of aromatic amines with unique substitution patterns. DFT studies, in combination with experimental results, suggest that the reaction occurs via base-mediated activation of HSA, followed by 1,2 aryl B-N migration. This mode of activation appears to be critical for the success of the reaction and allows, for the first time, a general, electrophilic amination of boronic acids at ambient temperature.

Microwave-assisted protection of primary amines as 2,5-dimethylpyrroles and their orthogonal deprotection

Primary amines can be readily doubly protected as N-substituted 2,5-dimethylpyrroles. Although this protecting group is stable toward strong bases and nucleophiles, long reaction times are required for both the protection and deprotection steps, generally resulting in low deprotection yields. By employing microwave irradiation, protection and deprotection reaction times are dramatically reduced. Furthermore, deprotection with dilute hydrochloric acid in ethanol increases reaction yields. Diverse deprotection conditions have been developed in conjunction with microwave irradiation, so that protection as an N-substituted 2,5-dimethylpyrrole can be orthogonal to other standard amine protecting groups, such as tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), and 9-fluorenylmethyloxycarbonyl (Fmoc).

Magnetically separable CuFe2O4 nanoparticles in PEG: A recyclable catalytic system for the amination of aryl iodides

A recyclable catalytic system comprising magnetically separable CuFe 2O4 nanoparticles in a poly(ethylene glycol) medium has been established as an inexpensive, nontoxic, environmentally benign system for the amination of aryl iodides with aqueous ammonia. A wide variety of aryl iodides underwent amination to afford the corresponding aryl amines in moderate to good yields. The catalytic system was recycled five times with consistent activity. Georg Thieme Verlag Stuttgart . New York.