610-17-3

Usage

Uses

N,N-Dimethyl-2-nitroaniline (cas# 610-17-3) is a compound useful in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1927, 1985 DOI: 10.1021/jo00211a028

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

Upstream product

• 874-52-2 N,N-dimethylaniline N-oxide 
• 121-69-7 N,N-dimethyl-aniline 
• 506-59-2 N,N-dimethylammonium chloride 
• 88-73-3 2-Chloronitrobenzene 
• 124-40-3 dimethyl amine 
• 67-56-1 methanol 
• 88-74-4 2-nitro-aniline 
• 74-88-4 methyl iodide 
• 528-29-0 1,2-Dinitrobenzene 
• 544-16-1 n-Butyl nitrite 
• 110-46-3 isopentyl nitrite 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 58669-01-5 6-(N-ethylamino)-3-methyluracil 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 89937-90-6 N-nitroso N-methyl-N-(2-nitroaniline) 
• 89-09-8 bis-(4-dimethylamino-3-nitro-phenyl)-methane 
• 1632-83-3 1-Methylbenzimidazole 
• 2836-03-5 N,N-dimethyl-1,2-phenylenediamine 
• 489-98-5 picramide 
• 829-02-7 4-Bromo-2-nitro-N,N-dimethylbenzeneamine 
• 89303-24-2 (5-Benzenesulfonylmethyl-2-nitro-phenyl)-dimethyl-amine 
• 89303-30-0 (3-Benzenesulfonylmethyl-2-nitro-phenyl)-dimethyl-amine 
• 139778-28-2 o-(Dimethylamino)phenyl hydrogen sulfate 
• 62764-95-8 C₈H₁₀N₂O₃ 
• 13351-73-0 1-methyl-1H-benzo[d][1,2,3]triazole 
• 614-00-6 N-methyl-N-nitrosoaniline 
• 612-28-2 2-nitro-N-methylaniline 
• 98-95-3 nitrobenzene 

Relevant academic research and scientific papers

Tert-amino effect-promoted rearrangement of aryl isothiocyanate: A versatile approach to benzimidazothiazepines and benzimidazothioethers

A general and practical approach to benzimidazothiazepine and benzimidazothioether derivatives via an intramolecular nucleophilic addition/ring expansion rearrangement of aryl isothiocyanates promoted by the tert-amino effect has been developed. This reaction is catalyzed by low-cost camphorsulfonic acid and tolerates a broad substrate scope with complete atom economy. Structurally intriguing benzimidazothiazepine and benzimidazothioether products could be easily obtained by a simple operation in good to excellent yield (up to 98%).

Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.

Mechanical force under the action of the nitration of aromatic compounds of nitrate method (by machine translation)

The invention discloses a mechanical force under the action of the nitration of aromatic compounds of nitrate method. The invention provides a method for preparing aromatic nitro compounds, comprising the following steps: under the action of mechanical force, aromatic compound with a metal nitrate or its hydrate by the nitration reaction, to obtain the aromatic nitro compound; the mechanical fastener is machinery offers can cause material physical and/or chemical nature of the change of the external force. The mechanical force can be compression, shear, impact, friction, tensile, bending and vibration of any kind. The invention has the following advantages: without the use of any solvent, thereby avoiding the waste liquid produced; and without the use of the acidic substance, the reaction is complete after treatment is simple, without any damage to the apparatus; a very high conversion and selectivity, can be applied to the nitration of conventional aromatic compound. (by machine translation)

Zinc Chloride Complexes with Aliphatic and Aromatic Guanidine Hybrid Ligands and Their Activity in the Ring-Opening Polymerisation of d,l-Lactide

The synthesis of the new hybrid guanidine ligands DMEGdmap, DMEGdeae, TMGdmab, DMEGdmab, TMGdeab and DMEGdeab is reported. These ligands were combined with zinc chloride, and the six obtained new complexes were structurally characterised by X-ray crystall

Two-photon "caging" groups: Effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups

High two-photon photolysis cross sections and water solubility of probes are important to avoid toxicity in biomedical applications of photolysis. Systematic variation of the position of a carboxyl electron-withdrawing group (EWG) on photolysis of 8-dimet

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

A unified strategy towards N-aryl heterocycles by a one-pot copper-catalyzed oxidative C-H amination of azoles

An efficient one-pot synthesis of N-aryl-substituted heterocycles by a Cu-catalyzed two-fold C-N bond formation is reported. This strategy involves a CuI-catalyzed C-N bond-forming reaction between azoles and electron-deficient bromopyridines followed by an intramolecular sp2 C-H amination. One of the products thus formed has been successfully used as a ligand for the synthesis of a Pd complex. An efficient one-pot synthesis of N-aryl heterocycles by a Cu-catalysed double C-N bond formation is reported. This strategy involves a CuI-catalysed C-N bond-forming reaction between azoles and electron-deficient bromopyridines followed by an intramolecular sp2 C-H amination.

Metal-free protodeboronation of electron-rich arene boronic acids and its application to ortho -functionalization of electron-rich arenes using a boronic acid as a blocking group

The metal-free thermal protodeboronation of various electron-rich arene boronic acids was studied. Several reaction parameters controlling this protodeboronation, such as solvent, temperature, and a proton source, have been investigated. On the basis of these studies, suitable reaction conditions for protodeboronation of several types of electron-rich arene boronic acids were provided. On the basis of this protodeboronation, a new protocol for the synthesis of ortho-functionalized electron-rich arenes from these boronic acids was developed using the boronic acid moiety as a blocking group in the electrophilic aromatic substitution reaction, followed by the removal of the boronic acid moiety via thermal protodeboronation. Mechanistic studies suggested that this protodeboronation might proceed via the complex formation of a boronic acid with a proton source, followed by the carbon-boron bond fission through σ-bond metathesis, to afford the corresponding arene compound and boric acid.