58259-34-0

Usage

Uses

Used in Dye Manufacturing Industry:
4-NITRO N-BUTYL ANILINE is used as a dye intermediate for the production of various dyes and pigments. Its chemical properties allow it to be a key component in the synthesis of a wide range of colorants used in different applications.
Used in Pigment Production:
In the pigment industry, 4-NITRO N-BUTYL ANILINE serves as a crucial intermediate in the creation of pigments. These pigments are utilized in various industries, including paints, coatings, plastics, and textiles, for their coloration and stability.
Used in Organic Compound Synthesis:
4-NITRO N-BUTYL ANILINE is also used as a building block in the synthesis of other organic compounds. Its unique structure makes it a valuable precursor for the development of new chemical entities with potential applications in various fields.
Safety Considerations:
Due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system, it is essential to handle 4-NITRO N-BUTYL ANILINE with care. Proper safety measures, including the use of personal protective equipment and adherence to safety protocols, should be in place when working with this chemical.

Upstream product

• 109-73-9 N-butylamine 
• 350-46-9 4-Fluoronitrobenzene 
• 21724-51-6 butyl-[1,2,4]triazol-4-yl-amine 
• 98-95-3 nitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 14368-49-1 p-nitrobenzenediazonium 
• 586-78-7 para-nitrophenyl bromide 
• 100-01-6 4-nitro-aniline 
• 100-02-7 4-nitro-phenol 
• 830-03-5 4-nitrophenol acetate 
• 109-69-3 n-Butyl chloride 
• 1516-60-5 4-nitrophenyl azide 
• 60669-69-4 di-n-butylboryl trifluoromethanesulfonate 
• 109-65-9 1-bromo-butane 

Downstream Products

• 123-72-8 butyraldehyde 
• 100-01-6 4-nitro-aniline 

Relevant academic research and scientific papers

Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling

With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.

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.

The Dependence of Ionic Liquid Solvent Effects on the Nucleophilic Heteroatom in SNAr Reactions. Highlighting the Potential for Control of Selectivity

Nucleophilic aromatic substitution (SNAr) reactions of 1-fluoro-4-nitrobenzene using similar nitrogen and sulfur nucleophiles were studied through extensive kinetic analysis in mixtures containing ionic liquids. The interactions of the ionic li

The invention relates to a N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method (by machine translation)

The invention discloses a to N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method, the method uses the aromatic halides with amine compound as a raw material, in order to alcohol compound as the solvent, in order to copper or copper compound as a catalyst, in order to as formula I or formula II as shown by a N, N - disubstituted hydrazide as a ligand, the presence of a base, in the 10 - 130 °C generating C - N coupled reaction for generating N - aryl compound: the invention mild reaction conditions, high chemical selectivity, substrate and wide range of application, simplicity of operation, product is simple and easy to separation and environmental protection, the obtained product yield is higher. Wherein R1, R2 is selected from methyl, phenyl, 4 - methoxyphenyl, 4 - nitro-phenyl, 2 - methylphenyl, 2 - isopropyl phenyl; R3 is hydrogen or methoxy. (by machine translation)

Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides

A general and effective CuI/N′,N′-diaryl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the amination of aryl iodides and bromides at room temperature with good chemoselectivity between -OH and -NH2 groups. Only 5 mol % of CuI and ligands was needed in this protocol to effect the amination of various aryl bromides and aryl iodides with a wide range of aliphatic and aryl amines (1.3 equiv).

Phenanthridin-6-one derivatives as the first class of non-steroidal pharmacological chaperones for Niemann-Pick disease type C1 protein

Niemann-Pick disease type C is a fatal, progressive neurodegenerative disease mostly caused by mutations in Nieamnn-Pick type C1 (NPC1), a late endosomal membrane protein that is essential for intracellular cholesterol transport. The most prevalent mutation, I1061T (Ile to Thr), interferes with the protein folding process. Consequently, mutated but intrinsically functional NPC1 proteins are prematurely degraded via proteasome, leading to loss of NPC1 function. Previously, we reported sterol derivatives as pharmacological chaperones for NPC1, and showed that these derivatives can normalize folding-defective phenotypes of I1061T NPC1 mutant by directly binding to, and stabilizing, the protein. Here, we report a series of compounds containing a phenanthridin-6-one scaffold as the first class of non-steroidal pharmacological chaperones for NPC1. We also examined their structure-activity relationships.

A process for the preparation method of the compound aromatic amines (by machine translation)

The invention discloses a method for preparing aromatic amine compounds, comprising the following steps: under protection of inert gas, with the ratio of the phenolic compound amine according to mole 1:2 - 40 are mixed and dissolved in the solvent, 50 - 140 °C reaction 6 - 15 hours, corresponding to preparing polymerizable aromatic amine compound, and then after treatment to obtain a pure aromatic amine compound. Raw materials of this invention generally are easy, simple operation, substrate and wide range of application, in the absence of catalyst under catalytic conditions of the phenolic compound can be obtained by nucleophilic addition reaction of the corresponding aromatic amine compound, and is suitable for industrial production. The present invention allows the presence of water in the reaction system, can be ammonia or hydrazine hydrate as the substrate, in order to ammonium chloride as a catalyst and a cosolvent, the success of the preparation to obtain a level from phenol hydroxy aromatic primary amino compound. The invention to phenol hydroxy has better selectivity, even if the presence of halogen atoms in the substrate does not affect the occurrence of the reaction. (by machine translation)

Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides

An efficient and highly practical procedure is reported for the Ullmann-Goldberg-type copper-catalyzed amination of aryl iodides. By using a combination of copper iodide and proline in the presence of an excess of an amine, a wide range of aryl iodides can be readily aminated at room temperature. The reaction proceeds well regardless of the electronic properties of the starting aryl iodide and the amination products can be obtained without the need for purification by column chromatography in most cases. Owing to its efficiency and the mildness of the reaction conditions, this amination could also be extended to the amination of complex aryl iodides at room temperature.

Cs2CO3-Promoted Direct N-Alkylation: Highly Chemoselective Synthesis of N-Alkylated Benzylamines and Anilines

Herein is described an efficient and chemoselective method for the synthesis of diversely substituted secondary amines in yields up to 98 %. Direct mono-N-alkylation of primary benzylamines and anilines with a wide range of alkyl halides is promoted by a cesium base in the absence of any additive or catalyst. The basicity and solubility of cesium carbonate in anhydrous N,N-dimethylformamide not only enables mono-N-alkylation of primary amines but also suppresses undesired dialkylation of the desired amines.

A recyclable Cu-catalyzed C-N coupling reaction in water and its application to synthesis of imidazo[1,2-a]quinoxaline

Polystyrene-supported pyrrole-2-carbohydrazide (PSP) was synthesized and combined with CuI to make up a recyclable heterogeneous catalytic system for Ullmann-type C-N coupling reaction in water. In which, a variety of functionalized aryl halides animated efficiently with anilines, benzylamine, aliphatic amines, and imidazole. its preliminary application resulted in a more practical synthesis of imidazo[1,2-a]quinoxaline.