3007-71-4

Usage

Uses

Used in Chemical Industry:
N-octylaniline is used as an intermediate in the production of dyes, antioxidants, and pharmaceuticals for its ability to react and form various chemical compounds.
Used in Lubricant Industry:
N-octylaniline is used as an oil additive to improve oxidation stability and corrosion inhibition in lubricants, enhancing the performance and longevity of the lubricants.
Used in Polyurethane Foam Industry:
N-octylaniline is used as a stabilizer in the formulation of polyurethane foam, contributing to the stability and quality of the foam during production.
However, exposure to N-octylaniline has been associated with potential health hazards, including skin and eye irritation, and it should be handled and used with caution.

Upstream product

• 111-87-5 octanol 
• 142-04-1 aniline hydrochloride 
• 114201-82-0 N-octyl-toluene-4-sulfonanilide 
• 111-83-1 1-bromo-octane 
• 62-53-3 aniline 
• 103-70-8 Formanilid 
• 7438-05-3 1-azidooctane 
• 71-43-2 benzene 
• 95851-34-6 N-(octylidene)aniline 
• 124-13-0 Octanal 
• 98-95-3 nitrobenzene 
• 111-86-4 n-Octylamine 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 78575-76-5 N-Octylacetanilid 

Downstream Products

• 124-13-0 Octanal 
• 114201-82-0 N-octyl-toluene-4-sulfonanilide 
• 2567-54-6 chloro-acetic acid-(N-octyl-anilide) 
• 55239-84-4 C₁₅H₂₂ClNO 
• 83715-95-1 10-Octyl-3-phenyl-10H-pyrimido[4,5-b]quinoline-2,4-dione 
• 16245-79-7 4-octylaniline 
• 62-53-3 aniline 
• 1311478-33-7 C₃₆H₅₈N₄O₂ 
• 251476-87-6 2'-hydroxy-3,3-bis-trifluoromethyl-[1,1':3'1]terphenyl-5'-carboxylic acid (8-phenyl-octyl)-amide 
• 251477-39-1 N-(8-phenyl-octyl)-3,5-bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)-benzamide 
• 1167-42-6 toluene-4-sulfonic acid-(4-octyl-anilide) 
• 213190-22-8 Octyl-phenyl-dithiocarbamic acid methyl ester 

Relevant academic research and scientific papers

Anti-Markovnikov Addition of Anilines to Aliphatic Terminal Alkynes Catalyzed by an 8-Quinolinolato Rhodium Complex

Anti-Markovnikov addition of anilines to aliphatic terminal alkynes proceeded using an 8-quinolinolato rhodium/phosphine catalyst system. The use of a strong organic base, 1,1,3,3,–tetramethylguanidine, in the catalyst system enabled the formation of the aldimine products. Substrates with various functional groups including polar groups such as a phenolic hydroxy group are applicable to the hydroamination.

Synthesis of an Fe-Pd bimetallic catalyst for: N -alkylation of amines with alcohols via a hydrogen auto-transfer methodology

Hydrogen auto-transfer (HAT) or borrowing hydrogen (BH) methodology which combines dehydrogenation, intermediate reaction and hydrogenation, is recognized as an excellent strategy for one-pot synthesis from an economic and environmental point of view. Although much effort has been made on the development of catalysts for HAT reactions, harsh conditions, external base or large amounts of noble metals are still required in most reported catalysis systems, and thus the exploration of a highly efficient and recyclable heterogeneous catalyst remains meaningful. In this work, a novel bimetallic catalyst, Fe10Pd1/NC500 derived from bimetallic MOF NH2-MIL-101(Fe10Pd1), has been prepared, and the catalyst exhibits superior catalytic performance for the N-alkylation of amines with alcohols via a hydrogen auto-transfer methodology. High yields of the desired products were achieved at 120 °C with an alcohol/amine molar ratio of 2?:?1 and required no external additive or solvent. A distinct enhancement in catalytic performance is observed when compared with monometallic catalysts, which can be ascribed to the "synergistic effects"inside the bimetallic alloys. The N-doped carbon support has been revealed to provide the necessary basicity which avoids the requirement of an external base. Moreover, a wide substrate range and remarkable reusability have been shown by Fe10Pd1/NC500, and this work highlights new possibilities for bimetallic catalysts applied in sustainable chemistry.

Synthesis of NHC-Iridium(III) Complexes Based on N-Iminoimidazolium Ylides and Their Use for the Amine Alkylation by Borrowing Hydrogen Catalysis

Anionic NHC ligands recently developed in our group, derived from N-iminoimidazolium ylides, were used to synthesize NHC-iridium(III) complexes. Their catalytic activities were evaluated in the amine alkylation of anilines using borrowing hydrogen catalysis. The high-yielding synthesis of a small library of complexes allowed a rapid screening of the ideal steric bulk of the NHC unit and basicity of the anionic tether for the investigated model reaction. A bulky aromatic N group on the imidazolidene moiety is required to achieve high catalytic activity, and the latter is proportional to the basicity of the anionic group. A selected substrate scope of the reaction was performed, providing fair to excellent yields of the desired alkylated anilines.

Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment

An example of homogeneous Mo-catalyzed direct N-alkylation of anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective N-alkylation of anilines or challenging nitroarenes with alcohols. The enhanced hydride-donating strategy should be useful in designing highly active systems for borrowing hydrogen transformations.

Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines

Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.

Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex

Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.

Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation

Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.

Dirhodium-Catalyzed Chemo-and Site-Selective C-H Amidation of N, N-Dialkylanilines

A method for dirhodium-catalyzed C(sp 3)-H amidation of N, N-dimethylanilines was developed. Chemoselective C(sp 3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp 2)-H bonds of the electron-rich aromatic ring. Site-selective C(sp 3)-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-Alkylaniline derivatives with secondary, tertiary, and benzylic C(sp 3)-H bonds α to a nitrogen atom.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

A highly efficient Co-based catalyst fabricated by coordination-assisted impregnation strategy towards tandem catalytic functionalization of nitroarenes with various alcohols

A well-defined hexamethylenetetramine (abbreviated as HMTA) based two-dimensional (2D) MOFs metalloligand (termed Zn-HMTA), with free uncoordinated tertiary amine groups, has been synthesized via solution diffusion method for the first time. The crystal structure of 2D Zn-HMTA metalloligand was determined by the single crystal X-ray diffraction (SCXRD). The SCXRD and X-ray photoelectron spectroscopy (XPS) analyses have revealed that the 2D Zn-HMTA metalloligand is rich in- free tertiary amine groups, which are of strong coordination ability to transition metal ions (e.g. Ni2+, Co2+, Zn2+, Cu2+). As a result, a 2D bimetallic Co@Zn-HMTA MOFs was synthesized via coordination-assisted impregnation (CAI) strategy attributed to the unique feature of strong coordinated ability of free tertiary amine groups. Furthermore, a series of self-supported Co-ZnO-CN nanocatalysts were afforded upon the as-synthesized Co@Zn-HMTA MOFs served as a self-sacrificial template for pyrolysis at different temperatures. The optimized catalyst (termed as Co-ZnO@CN-CAI) demonstrated the excellent catalytic performance for hydrogenation-alkylation tandem reaction in comparison with the classic ZnO@CN composite (derived from Zn-HMTA MOFs) supported metallic Co catalyst (Co-ZnO@CN-IWI) prepared by incipient wetness impregnation method. Moreover, the kinetic study was also performed to confirm that the alkylation is the rate-determining step in the hydrogenation-alkylation tandem reaction. The origin of enhanced catalytic performance of Co-ZnO@CN-CAI and the role of Co@Zn-HMTA MOFs precursor have been explored by way of various characterizations, e.g. HADDF-STEM-EDS, SEM-EDS, 13C MAS NMR, XRD, Raman and XPS, etc. It is anticipated that the prepared low-cost and easily prepared 2D Zn-HMTA metalloligand will become a general template for synthesis of highly self-supported catalysts with coordination-assisted impregnation strategy (CAI) for various catalytic reactions.