769-92-6

Basic information

• Product Name: 4-tert-Butylaniline
• Synonyms: TIMTEC-BB SBB007738;BUTTPARK 44\03-77;BENZENAMINE, 4-(1,1-DIMETHYLETHYL)-;4-TERT-BUTYLANILINE;4-tert-Butylaniline,99%;4-TERT-BUTYL BENZENEAMINE;1-Amino-4-tert-butylbenzene;4-tert-Butylaniline 98%
• CAS NO: 769-92-6
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 212-215-9
• Product Categories: Drug Intermediates;Aromatics;Amines;Phenyls & Phenyl-Het;C9 to C10;Nitrogen Compounds
• Mol File: 769-92-6.mol

Chemical Properties

• Melting Point: 15-16 °C(lit.)
• Boiling Point: 90-93 °C3 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: Clear orange-red to brownish/Liquid
• Density: 0.937 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0431mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: 0-10°C
• PKA: pK1: 3.78(+1) (25°C)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 2205786
• CAS DataBase Reference: 4-tert-Butylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-Butylaniline(769-92-6)
• EPA Substance Registry System: 4-tert-Butylaniline(769-92-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 769-92-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-tert-Butylaniline is used as a chemical intermediate for the synthesis of various compounds, such as formic acid-(4-tert-butyl-anilide), 4-tert-Butyl-4',4'-dinitrotriphenylamine, and 2-oxopyrimido[4,5-d]pyrimidin-5(6H)-one. These synthesized compounds have potential applications in various industries, including pharmaceuticals, materials science, and chemical research.
Used in Schiff Base Formation:
In the field of organic chemistry, 4-tert-Butylaniline is used in the formation of Schiff bases, specifically through a reaction with 4-tert-butylbenzaldehyde in ethanol. This reaction has been carried out using the matrix-assisted laser desorption ionization-chip system, which is a technique for the analysis of large biomolecules.
Overall, 4-tert-Butylaniline serves as a valuable compound in the chemical industry due to its ability to participate in various reactions and synthesize a range of products with potential applications in different sectors.

InChI:InChI=1/C10H15N/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7H,11H2,1-3H3/p+1

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 142-04-1 aniline hydrochloride 
• 98-54-4 para-tert-butylphenol 
• 62-53-3 aniline 
• 64-10-8 phenyl carbamate 
• 75-65-0 tert-butyl alcohol 
• 20330-45-4 4-tert-butylacetanilide 
• 253185-03-4 tert-butylbenzene 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 558-17-8 tert-Butyl iodide 
• 98-95-3 nitrobenzene 
• 937-33-7 N-tert-butylaniline 
• 479533-85-2 1-(4-tert-butylphenyl)-3-phenylthiourea 
• 3972-65-4 1-bromo-4-tert-butylbenzene 

Downstream Products

• 93721-24-5 4-tert-butyl-N,N-bis-(2-hydroxy-ethyl)-aniline 
• 63429-97-0 N-(4-(tert-butyl)phenyl)formamide 
• 68714-39-6 N,N'-bis-(4-tert-butyl-phenyl)-thiourea 
• 4627-22-9 bis(4-tert-butylphenyl)amine 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 31951-12-9 4-tert-butyl-3-nitro-phenylamine 
• 4365-63-3 2‐((4‐(tert‐butyl)phenyl)thio)acetic acid 
• 100134-03-0 4-tert-butylphenyl phosphonic acid 
• 20330-45-4 4-tert-butylacetanilide 
• 4572-48-9 N-(4-(tert-butyl)phenyl)naphthalen-1-amine 
• 59238-66-3 N-(4-(tert?butyl)phenyl)benzamide 
• 89735-36-4 N-(4-(tert-butyl)phenyl)-4-methylbenzamide 
• 95337-71-6 1-(1-(4-tert-butyl)phenyl)-4-yl-2,5-dimethyl-1H-pyrrole 
• 60377-30-2 4-[3-(4-tert-Butyl-phenylamino)-2-hydroxy-propoxy]-benzoic acid methyl ester 

Relevant articles and documents

Highly organic phase soluble polyisobutylene-bound cobalt phthalocyanines as recyclable catalysts for nitroarene reduction

A cobalt phthalocyanine (CoMPc) containing covalently linked polyisobutylene (PIB) groups as phase anchors that is both highly soluble in nonpolar organic solvents and phase selectively soluble in a liquid/liquid separation step is shown to be an effective recyclable homogeneous catalyst for nitroarene reduction in a semi-thermomorphic system. Electron-donating and electron-withdrawing substituents in the nitroarene are tolerated in this aniline synthesis and the catalyst is recyclable up to 10 cycles with little leaching and no detectable loss in reactivity after 10 cycles.

Synthesis and characterization of chitosan pyridyl imine palladium (CPIP) complex as green catalyst for organic transformations

In this work, the modification of chitosan using 2-acetyl pyridine has been used to prepare an intermediate, chitosan pyridyl imine (CPI), in first step and then in second step it is further reacted with Pd(OAc)2 to develop chitosan pyridyl imine palladium (CPIP) complex catalyst in a very simplistic way. The formed CPIP has been extensively characterized with respect to raw chitosan utilizing methods including FT-IR, pyrolysis GC–MS, XRD, XPS, FE-SEM, EDS, TGA-DTG and DSC. TG-DSC study suggested that the catalyst is thermally stable up to 300?°C. This catalyst shows an excellent activity in the reduction of toxic pollutant nitrobenzene to less toxic aniline. CPIP complex has also been found to give magnificent results in Suzuki–Miyaura and Heck cross-coupling reactions, and therefore, using this green catalyst, the toxic phosphine ligand can be excluded from cross-coupling reactions. This study furnishes an economic and eco-friendly catalyst for organic transformation in sustainable chemistry.

Development and Application of Efficient Ag-based Hydrogenation Catalysts Prepared from Rice Husk Waste

The development of strategies for the sustainable management and valorization of agricultural waste is of outmost importance. With this in mind, we report the use of rice husk (RH) as feedstock for the preparation of heterogeneous catalysts for hydrogenation reactions. The catalysts were prepared by impregnating the milled RH with a silver nitrate solution followed by carbothermal reduction. The composition and morphology of the prepared catalysts were fully assessed by IR, AAS, ICP-MS, XPS, XRD and STEM techniques. This novel bio-genic silver-based catalysts showed excellent activity and remarkable selectivity in the hydrogenation of nitro groups in both aromatic and aliphatic substrates, even in the presence of reactive functionalities like halogens, carbonyls, borate esters or nitriles. Recycling experiments showed that the catalysts can be easily recovered and reused multiple times without significant drop in performance and without requiring re-activation.

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

Method for synthesizing heteroatom- substituted aromatic compound from styrene compound

The invention discloses a method for synthesizing a heteroatom-substituted aromatic compound from a styrene compound, which comprises the following steps of: mixing a styrene compound with a general formula (I) and a heteroatom-containing compound with a general formula (II), and reacting in the presence of an acid additive and an organic solvent to obtain a heteroatom-substituted compound with ageneral formula (III). According to the synthesis method disclosed by the invention, a large amount of styrene compounds are used as raw materials and react to generate aromatic amine or phenol compounds under the action of no metal catalysis; and compared with the traditional aromatic amine and phenol synthesis method, the method has the advantages of high yield, simple conditions, low waste discharge amount, no metal participation, simple reaction equipment, easiness in industrial production and the like.

Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

Selective primary aniline synthesis through supported Pd-catalyzed acceptorless dehydrogenative aromatization by utilizing hydrazine

By utilizing hydrazine (N2H4) as the nitrogen source in the presence of a hydroxyapatite-supported Pd nanoparticle catalyst (Pd/HAP), various primary anilines can be selectively synthesized from cyclohexanonesviaacceptorless dehydrogenative aromatization. The strong nucleophilicity of N2H4and the stability of the hydrazone intermediates can effectively suppress the formation of the undesired secondary aniline byproducts.

Copper catalyzed reduction of azides with diboron under mild conditions

We report herein the first Cu catalyzed reduction of azides with B2pin2 (pin = pinacolato) as the reductant under very mild conditions. A series of primary amines and amides were obtained in moderate to excellent yields with high chemoselectivity and good functional group tolerance. This reaction can be performed with a cheap copper salt, a simple NHC ligand and a diboron reagent.

Mild environment-friendly oxidative debenzylation of N-benzylanilines using DMSO as an oxidant

Oxidative debenzylation of N-benzyl aromatic amines using DMSO as a non-toxic oxidant and catalyzed by TsOH gave Nphenylimines, which were spontaneously hydrolyzed to form anilines and benzaldehydes in good yields. This reaction employs mild, metal-free conditions. The conditions are also suitable for the debenzylation of benzylphenylethers.