104-13-2

Basic information

• Product Name: 4-n-Butylaniline
• Synonyms: Aniline, 4-butyl-;Aniline, p-butyl-;Benzenamine,4-butyl-;p-Aminobutylbenzene;p-Aminobutyl-benzene;p-butylaminobenzene;Butylaniline,98%;L-1,2,3-Tetrahhydroisoquinoline-3-Carboxylic Acid
• CAS NO: 104-13-2
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 203-177-4
• Product Categories: Intermediates of Dyes and Pigments;Anilines (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Amines;C9 to C10;Nitrogen Compounds
• Mol File: 104-13-2.mol

Chemical Properties

• Melting Point: -14°C
• Boiling Point: 133-134 °C14 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: Clear yellow to slightly brown/Liquid
• Density: 0.945 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.094mmHg at 25°C
• Refractive Index: n20/D 1.535(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.91±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 1447268
• CAS DataBase Reference: 4-n-Butylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-n-Butylaniline(104-13-2)
• EPA Substance Registry System: 4-n-Butylaniline(104-13-2)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: BW9470000
• TSCA: Yes
• Hazardous Substances Data: 104-13-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
4-Butylaniline is used as a precursor in the synthesis of various chemical compounds, such as dyes, pharmaceuticals, and agrochemicals. Its versatile structure allows for further functionalization and modification, making it a valuable building block in the chemical industry.
Used in Analytical Chemistry:
4-Butylaniline is used as a component in the fabrication of RP/ion-exchange, mixed-mode, and monolithic materials for capillary liquid chromatography (LC). These materials are essential for the separation and analysis of complex mixtures in various fields, including pharmaceuticals, environmental science, and biotechnology.
Used in Material Science:
Due to its unique chemical properties, 4-Butylaniline can be employed in the development of novel materials with specific characteristics, such as improved solubility, stability, or reactivity. This makes it a valuable asset in the field of material science, where the design and synthesis of new materials are of great importance.

Biochem/physiol Actions

4-Butylaniline is a mammalian retinoid cycle inhibitor that reversibly suppresses the recovery of the outward R(2) component of ERC (early receptor current) from Vitamin A and 11-cis-retinal-loaded cells.

InChI:InChI=1/C10H15N/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8,10H,2,6,11H2,1H3

Upstream product

• 20651-75-6 1-butyl-4-nitro-benzene 
• 1126-78-9 N-(n-butyl)aniline 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 2492-82-2 N-butylanilinium chloride 
• 62-53-3 aniline 
• 71-36-3 butan-1-ol 
• 142-04-1 aniline hydrochloride 
• 73000-50-7 [10-(4-{[(E)-4-Butyl-phenylimino]-methyl}-phenoxy)-decyl]-trimethyl-ammonium; bromide 
• 73000-46-1 (4-{[(Z)-4-Butyl-phenylimino]-methyl}-phenyl)-trimethyl-ammonium; bromide 
• 73000-47-2 [4-(4-{[(Z)-4-Butyl-phenylimino]-methyl}-phenoxy)-butyl]-trimethyl-ammonium; bromide 
• 2749-11-3 (S)-Alaninol 
• 26227-73-6 N-(4-methoxybenzylidene)-4-(n-butyl)aniline 
• 5856-62-2 (S)-2-aminobutan-1-ol 
• 2026-48-4 (S)-valinol 

Downstream Products

• 42980-14-3 1,4-bis-(4-butyl-anilino)-anthraquinone 
• 4946-15-0 4-butylthiophenol 
• 41492-05-1 p-bromobutylbenzene 
• 61644-32-4 4-butyl-3-nitroaniline 
• 3663-20-5 N-(4-butylphenyl)acetamide 
• 100369-67-3 N-(4-butyl-phenyl)-glycine 
• 7634-74-4 6-n-butylquinoline 
• 13330-29-5 4-n-butyl-N,N-dimethylaniline 
• 137273-36-0 N-methyl-4-n-butylaniline 
• 69984-83-4 (4-butyl-phenyl)-(6-methanesulfinyl-[1,3,4]thiadiazolo[2,3-c][1,2,4]thiadiazol-3-ylidene)-amine 
• 67330-58-9 4-Butyl-2,6-diethyl-phenylamine 
• 22505-15-3 N-(4-Butyl-phenyl)-N'-(4-ethoxy-phenyl)-oxalamide 
• 31520-42-0 (4-butyl-phenyl)-(4,5,6,7-tetrahydro-[1,3]thiazepin-2-yl)-amine 
• 71260-66-7 2,2,2-Tribromoethyl-phospho-(4-butylanilido)-chloridat 

Relevant articles and documents

Nematic to smectic texture transformation in MBBA by in situ synthesis of silver nanoparticles

The present study describes the texture changes in 'nematic' N-(4-methoxybenzylidene)-4-butylaniline (MBBA) by in situ synthesis of silver nanoparticles in the system without any external reducing or stabilizing agents. Optical polarizing microscopy (OPM), differential scanning calorimetry (DSC), nuclear magnetic resonance (NMR) spectroscopy, Fourier-transform infrared (FT-IR) spectroscopy, and scanning and transmission electron microscopy (SEM and TEM) were utilized to understand the mechanistic details of the texture transformation in MBBA. The experimental results collectively suggest that the silver nanoparticles are generated through the reduction of silver ions by MBBA upon heat treatment, followed by a clear texture transformation from 'nematic' to 'smectic'. The 'smectic' MBBA - Ag NP conjugate forms a stable luminescent glassy phase on rapid cooling, with an emission maximum of 500 nm upon photo-excitation at the silver plasmon absorption. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2010.

Dibenzothiophene Sulfoximine as an NH3 Surrogate in the Synthesis of Primary Amines by Copper-Catalyzed C?X and C?H Bond Amination

Readily accessible dibenzothiophene sulfoximine is an NH3 surrogate allowing the preparation of free anilines by copper-catalyzed cross-coupling reactions with aryl iodides or amides followed by radical S?N bond cleavage. The one-pot/two-step r

Electric-field modulation of component exchange in constitutional dynamic liquid crystals

(Figure Presented) Playing the field: Application of an electric field to the thermodynamic equilibria of constitutionally dynamic sets of imines and amines that contain an imine with liquid-crystalline properties and a negative dielectric anisotropy leads to the amplification of the constituent that couples most strongly to the electric field, namely the liquid crystal (LC, see example). The field can thus induce a liquid to nematic phase transition.

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation

A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]

Superhydrophobic nickel/carbon core-shell nanocomposites for the hydrogen transfer reactions of nitrobenzene and N-heterocycles

In this work, catalytic hydrogen transfer as an effective, green, convenient and economical strategy is for the first time used to synthesize anilines and N-heterocyclic aromatic compounds from nitrobenzene and N-heterocycles in one step. Nevertheless, how to effectively reduce the possible effects of water on the catalyst by removal of the by-product water, and to further introduce water as the solvent based on green chemistry are still challenges. Since the structures and properties of carbon nanocomposites are easily modified by controllable construction, a one step pyrolysis process is used for controllable construction of micro/nano hierarchical carbon nanocomposites with core-shell structures and magnetic separation performance. Using various characterization methods and model reactions the relationship between the structure of Ni?NCFs (nickel-nitrogen-doped carbon frameworks) and catalytic performance was investigated, and the results show that there is a positive correlation between the catalytic performance and hydrophobicity of catalysts. Besides, the possible catalytically active sites, which are formed by the interaction of pyridinic N and graphitic N in the structure of nitrogen-doped graphene with the surfaces of Ni nanoparticles, should be pivotal to achieving the relatively high catalytic performance of materials. Due to its unique structure, the obtained Ni?NCF-700 catalyst with superhydrophobicity shows extraordinary performances toward the hydrogen transfer reaction of nitrobenzene and N-heterocycles in the aqueous state; meanwhile, it was also found that Ni?NCF-700 still retained its excellent catalytic activity and structural integrity after three cycles. Compared with traditional catalytic systems, our catalytic systems offer a highly effective, green and economical alternative for nitrobenzene and N-heterocycle transformation, and may open up a new avenue for simple construction of structure and activity defined carbon nanocomposite heterogeneous catalysts with superhydrophobicity.

Catalytic synthesis method of p-n-butylaniline

The invention relates to the field of organic synthesis, and discloses a catalytic synthesis method of p-n-butylaniline. The catalytic synthesis method comprises the following steps that (1) aniline,butanol and acid modified graphite phase carbon nitride are placed in a reactor, the temperature is raised to 150-170 DEG C, and is kept for areaction for 5-7 h; (2) then the temperature is raised to230-250 DEG C, and is kept for a reaction for 9-11 h; and (3) a reactant is taken for reflux in alkali liquor, and is separated and dried to obtain a crude product of the p-n-butylaniline. According to the catalytic synthesis method, the acid-modified graphite phase carbon nitride is used as a catalyst for the synthesis reaction of the p-n-butylaniline, the good catalytic activity is achieved, theyield of the p-n-butylaniline is high, meanwhile the acid-modified graphite phase carbon nitride is very environment-friendly, non-toxic and pollution-free, corrosion and damage to equipment are avoided, and an environment-friendly catalyst is achieved.

From alkylarenes to anilines via site-directed carbon–carbon amination

Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.

Aromatic amine compound synthesis method

The invention discloses an aromatic amine compound synthesis method which is characterized in that the method is implemented according to any of two methods. The first method includes the steps: mixing an alkyl aromatic compound with a general formula (I) and a nitrogen-containing compound with a general formula (II); performing reaction on mixture under an oxidizing agent and an organic solvent to obtain an aromatic amine compound with a general formula (III). The second method includes the steps: mixing an aromatic alcohol derivative with a general formula (I') and the nitrogen-containing compound with the general formula (II); performing reaction on mixture under an acid additive and an organic solvent to prepare the aromatic amine compound with the general formula (III). According to the method, a lot of alkyl aromatic compounds or aromatic alcohol derivatives firstly serve as raw materials, and the raw materials are reacted to generate the aromatic amine compound without the action of metal catalysis. Compared with a traditional synthesis method, the synthesis method has the advantages that the method is high in yield and simple in condition, waste discharging amount is less,metal participation is omitted, a reaction device is simple, industrial production is easily achieved and the like. The method has a wide application prospect.

Synthesis of 4 - n-alkyl substituted phenol method

The invention discloses a synthesis method of 4-n-alkyl substituted phenol. Under the catalysis of zinc chloride, aniline and n-alkyl alcohol with the carbon number being 4-30 react in methylbenzene or xylene to obtain the 4-n-alkyl substituted aniline, and then the 4-n-alkyl substituted aniline reacts with sodium nitrite and acid to obtain the 4-n-alkyl substituted phenol. The synthesis method is easy to implement, an intermediate directly enters the next reaction without being separated or purified, and therefore the reaction efficiency is improved. The final product is high in purity and is good in depth of parallelism when reappearing, and technological conditions are suitable for mass production.