60995-75-7

Usage

Uses

Used in Chemical Synthesis:
N-BUTYL-M-TOLUIDINE is used as a catalyst and process solvent in various chemical reactions, facilitating the synthesis of a wide range of organic compounds.
Used in Dye and Pigment Production:
As an intermediate, N-BUTYL-M-TOLUIDINE plays a crucial role in the production of dyes and pigments, contributing to the coloration of various materials.
Used in Pharmaceutical Industry:
N-BUTYL-M-TOLUIDINE is employed as a chemical intermediate in the synthesis of pharmaceuticals, aiding in the development of new drugs and medications.
Used in Lubricant Additives:
N-BUTYL-M-TOLUIDINE is used as an additive in lubricants to enhance their performance and improve the efficiency of machinery and engines.
Used in Antioxidant Production:
N-BUTYL-M-TOLUIDINE is utilized in the production of antioxidants, which are essential in preventing the oxidation of materials and extending their shelf life.
Safety Precautions:
Due to the potential health risks associated with N-BUTYL-M-TOLUIDINE, it is imperative to handle and store this chemical with proper safety measures. This includes wearing protective gear, ensuring proper ventilation, and following guidelines for safe handling and disposal to prevent any adverse health effects.

InChI:InChI=1/C11H17N/c1-3-4-8-12-11-7-5-6-10(2)9-11/h5-7,9,12H,3-4,8H2,1-2H3

Upstream product

• 542-69-8 1-iodo-butane 
• 108-44-1 1-amino-3-methylbenzene 
• 69833-26-7 N-(m-tolyl)butyramide 
• 1643-19-2 tetrabutylammomium bromide 
• 625-95-6 3-Iodotoluene 
• 109-73-9 N-butylamine 
• 108-41-8 1-chloro-3-methylbenzene 
• 109-74-0 propyl cyanide 
• 99-08-1 1-methyl-3-nitrobenzene 
• 123-72-8 butyraldehyde 
• 10174-66-0 N¹,N³-dibutylmalonamide 
• 591-17-3 meta-bromotoluene 
• 71-36-3 butan-1-ol 
• 109-65-9 1-bromo-butane 

Downstream Products

• 101775-79-5 1-butyl-7-methyl-1,2,3,4-tetrahydro-quinolin-3-ol 
• 97962-51-1 3-(N-Butyl-3-methylanilino)-4-chlor-3-cyclobuten-1,2-dion 
• 123-72-8 butyraldehyde 
• 108-44-1 1-amino-3-methylbenzene 
• 46420-19-3 4'-acetoxy-3'-methylacetanilide 
• 537-92-8 3-Methylacetanilide 
• 1307740-88-0 2-(4-butylamino-2-methylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol 
• 1307740-59-5 5-butyl-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methylphenanthridin-6(5H)-one 
• 1307740-98-2 N-butyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methylphenyl]-2-iodobenzamide 
• 67103-36-0 C₂₂H₂₄N₂O₄ 
• 55240-18-1 C₁₂H₁₆ClNO 

Relevant academic research and scientific papers

Efficient nickel-catalysed: N -alkylation of amines with alcohols

The selective N-alkylation of amines with alcohols via the borrowing hydrogen strategy represents a prominent sustainable catalytic method, which produces water as the only by-product and is ideally suited for the catalytic transformation of widely available alcohol reaction partners that can be derived from renewable resources. Intensive research has been devoted to the development of novel catalysts that are mainly based on expensive noble metals. However, the availability of homogeneous or heterogeneous non-precious metal catalysts for this transformation is very limited. Herein we present a highly active and remarkably easy-to-prepare Ni based catalyst system for the selective N-alkylation of amines with alcohols, that is in situ generated from Ni(COD)2 and KOH under ligand-free conditions. This novel method is very efficient for the functionalization of aniline and derivatives with a wide range of aromatic and aliphatic alcohols as well as diols and exhibits excellent functional group tolerance including halides, benzodioxane and heteroaromatic groups. Several TEM measurements combined with elemental analysis were conducted in order to gain insight into the nature of the active catalyst and factors influencing reactivity.

Manganese catalyzed N-alkylation of anilines with alcohols: Ligand enabled selectivity

Ligand enabled Earth-abundant manganese catalyzed N-alkylation of amines with alcohols via a hydrogen auto-transfer strategy is reported. The choice of the ligand plays a significant role in the alcohol reactivity (aliphatic or aromatic) toward N-alkylation reactions.

Synthesis of quinoline derivatives from anilines and aldehydes catalyzed by Cp2ZrCl2 and recyclable Cp2ZrCl2/MCM-41 system

A facile method for the synthesis of quinoline derivatives using catalytic amount of Cp2ZrCl2 or Cp2ZrCl2 supported on MCM-41 (Cp2ZrCl2/MCM-41) in reaction of anilines and aldehydes is described. When Cp2ZrCl2/MCM-41 was used as catalyst, the yields of quinolines were enhanced by 5-15% compared with Cp2ZrCl2 as catalyst alone under the same reaction conditions. More importantly, Cp2ZrCl2/MCM-41 catalyst can be reused at least thrice by simple recover via filtration in air. Moreover, both Cp2ZrCl2 and Cp2ZrCl2/MCM-41 showed good catalytic activities to generate corresponding quinoline derivatives in moderate to good yields by varying the substituent of aniline and aldehyde. And the reaction conditions were optimized by studying the influences of reactant ratio, additives, solvent effect and reaction temperatures.

Development of Quinoline-2,4(1H,3H)-diones as Potent and Selective Ligands of the Cannabinoid Type 2 Receptor

The cannabinoid type 2 receptors (CB2Rs) play crucial roles in inflammatory diseases. There has been considerable interest in developing potent and selective ligands for CB2R. In this study, quinoline-2,4(1H,3H)-dione analogs have been designed, synthesized, and evaluated for their potencies and binding properties toward the cannabinoid type 1 receptor (CB1R) and CB2R. C5- or C8-substituted quinoline-2,4(1H,3H)-diones demonstrate CB2R agonist activity, while the C6- or C7-substituted analogs are antagonists of CB2R. In addition, oral administration of 21 dose-dependently alleviates the clinical symptoms of experimental autoimmune encephalomyelitis in a mouse model of multiple sclerosis and protects the central nervous system from immune damage. Furthermore, the interaction modes predicted by docking simulations and the 3D-QSAR model generated with CoMFA may offer guidance for further design and modification of CB2R modulators.

T-BuXPhos: A highly efficient ligand for Buchwald-Hartwig coupling in water

An efficient and versatile 'green' catalytic system for the Buchwald-Hartwig cross-coupling reaction in water is reported. In an aqueous micellar medium, the combination of t-BuXPhos with [(cinnamyl)PdCl]2 showed excellent performance for coupling arylbromides or chlorides with a large set of amines, amides, ureas and carbamates. The method is functional-group tolerant, proceeds smoothly (30 to 50 °C) and provides rapid access to the target compounds in good to excellent isolated yields. When applied to the synthesis of a known NaV1.8 modulator, this method led to a significant improvement of the E-factor in comparison with classical organic synthesis. the Partner Organisations 2014.

Copper(I)-catalyzed N-arylation of N1,N3- dibenzylmalonamide and N1,N3-dibutylmalonamide followed by cleavage of the malonyl group with aryl halides under ligand-free conditions

We primarily developed a practical and convenient protocol to synthesize of aromatic amines based on CuI-catalyzed N-arylation of N1,N 3-dibenzylmalonamide and N1,N3- dibutylmalonamide followed by cleavage of the malonyl group with aryl halides under ligand-free conditions giving good yields.

Copper-mediated aryl amination: In situ generation of an active copper(I) species

We have developed novel conditions for copper-mediated aryl amination by using a combination of easy-to-handle and inexpensive Cu(OAc) 2·H2O and phenylhydrazine. Georg Thieme Verlag Stuttgart . New York.

A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc

A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.

One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes

(Chemical Equation Presented) One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using various aldehydes by Pd/C catalyst in aqueous 2-propanol solvent with ammonium formate as in situ hydrogen donor is illustrated. The reaction proceeded smoothly and selectively with excellent yield at room temperature. Our protocol presents a facile, economical, and environmentally benign alternative for reductive amination.

Reductive monoalkylation of aromatic and aliphatic nitro compounds and the corresponding amines with nitriles

(Chemical Equation Presented) A simple, selective, rapid, and efficient procedure for the synthesis of secondary amines from the reductive alkylation of either aliphatic or aromatic nitro compounds and the corresponding amines is reported. Ammonium formate is used as the hydrogen source and Pd/C as the hydrogen transfer catalyst. The reaction is carried out at room temperature. The rate differences for the preferential formation of secondary over tertiary products are due to both steric and electronic factors.