15799-79-8

Basic information

• Product Name: 3-Dimethylaminoanisole
• Synonyms: N,N-DIMETHYL-M-ANISIDINE;N1,N1-DIMETHYL-3-METHOXYANILINE;3-DIMETHYLAMINOANISOLE;3-METHOXY-N,N-DIMETHYLANILINE;3-Methoxy-N,N-dimethylbenzeneamine;N,N-Dimethyl-m-anisidine~3-Methoxy-N,N-dimethylaniline;3-DIMETHYLAMINOANISOLE 98%;m-(Dimethylamino)anisole
• CAS NO: 15799-79-8
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 15799-79-8.mol

Chemical Properties

• Boiling Point: 113-114 °C (6 mmHg)
• Flash Point: 113-114°C/6mm
• Appearance: clear yellow liquid
• Density: 1.031
• Vapor Pressure: 0.174mmHg at 25°C
• Refractive Index: 1.5575-1.5595
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4?+-.0.10(Predicted)
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 1423591
• CAS DataBase Reference: 3-Dimethylaminoanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Dimethylaminoanisole(15799-79-8)
• EPA Substance Registry System: 3-Dimethylaminoanisole(15799-79-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37/39-26-23
• RIDADR: 2810
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 15799-79-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Dimethylaminoanisole is used as an active pharmaceutical ingredient for its antineoplastic properties, contributing to the development of treatments for cancer. Its ability to inhibit tumor growth and potentially synergize with conventional chemotherapeutic drugs enhances its value in this application.
Used in Chemical Synthesis:
3-Dimethylaminoanisole is used as a key intermediate in the synthesis of various organic compounds, such as C20H19NO4. It plays a crucial role in chemical reactions, requiring reagent tributyl orthoformate and solvent propan-2-ol with a reaction time of 90 minutes to produce the desired product.
Used in Antimicrobial Applications:
Due to its antibacterial properties, 3-Dimethylaminoanisole can be employed in the development of antimicrobial agents, useful in various industries such as healthcare, agriculture, and water treatment. Its ability to combat bacterial growth can contribute to the creation of more effective and targeted treatments against bacterial infections.

InChI:InChI=1/C9H13NO/c1-10(2)8-5-4-6-9(7-8)11-3/h4-7H,1-3H3

Upstream product

• 64-18-6 formic acid 
• 555-03-3 3-nitroanisole 
• 50-00-0 formaldehyd 
• 536-90-3 m-Anisidine 
• 109-79-5 n-butanethiol 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 53290-32-7 m-MeOC₆H₄NMe₃(+)*I(-) 
• 616-38-6 carbonic acid dimethyl ester 
• 591-27-5 m-Hydroxyaniline 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 124-38-9 carbon dioxide 
• 14318-66-2 3-methoxy-N-methylaniline 

Downstream Products

• 880470-13-3 [4-(dimethylamino)-2-methoxyphenyl](phenyl)-N-[(2-pyridyl)sulfonyl]methanamine 
• 447461-92-9 (R)-4-benzoyloxy-3-(4-dimethylamino-2-methoxy-phenyl)-butyraldehyde 
• 84562-49-2 2,6-Dichloro-N'-[1-(4-dimethylamino-2-methoxy-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 85103-69-1 2,6-dichloro-N'-(4-dimethylamino-2-methoxybenzyl)-p-phenylenediamine 
• 85103-68-0 N'-[2,6-Dichloro-4-(4-dimethylamino-2-methoxy-benzylamino)-phenyl]-N,N-dimethyl-formamidine 
• 95555-45-6 2,2'-dimethoxy-tetra-N-methyl-trans-stilbene-4,4'-diyldiamine 
• 447462-76-2 (S)-3-(4-Dimethylamino-2-methoxy-phenyl)-3-phenyl-propanol 
• 447462-08-0 (R)-4-oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester 
• 447462-79-5 (S)-3-(4-dimethylamino-2-methoxy-phenyl)-3-phenylpropanol tert-butyldimethylsilyl ether 

Relevant articles and documents

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Trialkylammonium salt degradation: Implications for methylation and cross-coupling

Trialkylammonium (most notably N,N,N-trimethylanilinium) salts are known to display dual reactivity through both the aryl group and the N-methyl groups. These salts have thus been widely applied in cross-coupling, aryl etherification, fluorine radiolabelling, phase-transfer catalysis, supramolecular recognition, polymer design, and (more recently) methylation. However, their application as electrophilic methylating reagents remains somewhat underexplored, and an understanding of their arylation versus methylation reactivities is lacking. This study presents a mechanistic degradation analysis of N,N,N-trimethylanilinium salts and highlights the implications for synthetic applications of this important class of salts. Kinetic degradation studies, in both solid and solution phases, have delivered insights into the physical and chemical parameters affecting anilinium salt stability. 1H NMR kinetic analysis of salt degradation has evidenced thermal degradation to methyl iodide and the parent aniline, consistent with a closed-shell SN2-centred degradative pathway, and methyl iodide being the key reactive species in applied methylation procedures. Furthermore, the effect of halide and non-nucleophilic counterions on salt degradation has been investigated, along with deuterium isotope and solvent effects. New mechanistic insights have enabled the investigation of the use of trimethylanilinium salts in O-methylation and in improved cross-coupling strategies. Finally, detailed computational studies have helped highlight limitations in the current state-of-the-art of solvation modelling of reaction in which the bulk medium undergoes experimentally observable changes over the reaction timecourse. This journal is

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Compound used as blue pressure-sensitive dye and preparation method and application thereof

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Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis

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Benzo polyaza and phosphole oxygen ligand and complex containing same, preparation method and application

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Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides

The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.

Efficient and Selective N-Methylation of Nitroarenes under Mild Reaction Conditions

Herein, we report a straightforward protocol for the preparation of N,N-dimethylated amines from readily available nitro starting materials using formic acid as a renewable C1 source and silanes as reducing agents. This tandem process is efficiently accomplished in the presence of a cubane-type Mo3PtS4 catalyst. For the preparation of the novel [Mo3Pt(PPh3)S4Cl3(dmen)3]+ (3+) (dmen: N,N′-dimethylethylenediamine) compound we have followed a [3+1] building block strategy starting from the trinuclear [Mo3S4Cl3(dmen)3]+ (1+) and Pt(PPh3)4 (2) complexes. The heterobimetallic 3+ cation preserves the main structural features of its 1+ cluster precursor. Interestingly, this catalytic protocol operates at room temperature with high chemoselectivity when the 3+ catalyst co-exists with its trinuclear 1+ precursor. N-heterocyclic arenes, double bonds, ketones, cyanides and ester functional groups are well retained after N-methylation of the corresponding functionalized nitroarenes. In addition, benzylic-type as well as aliphatic nitro compounds can also be methylated following this protocol.

Base-oxidant promoted metal-free N-demethylation of arylamines

A metal-free oxidative N-demethylation of arylamines with triethylamine as a base and tert-butyl hydroperoxide (TBHP) as oxidant is reported in this paper. The reaction is general, practical, inexpensive, non-toxic, and the method followed is environmentally benign, with moderate to good yields. [Figure not available: see fulltext.]