6310-21-0

Basic information

• Product Name: 2-tert-Butylaniline
• Synonyms: 2-TERT-BUTYLANILINE;AKOS BBS-00003572;Aniline, 2-tert-butyl-;2-TERT-BUTYLPHENYLAMINE;2-(1,1-Dimethylethyl)benzenamine;2-tert-Butylbenzenamine;2-tert-Butylaniline,99%;2-tert-Butylaniline 98%
• CAS NO: 6310-21-0
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 228-634-5
• Product Categories: Aromatics;Anilines, Aromatic Amines and Nitro Compounds;Amines;C9 to C10;Nitrogen Compounds
• Mol File: 6310-21-0.mol

Chemical Properties

• Melting Point: −60 °C(lit.)
• Boiling Point: 123-124 °C17 mm Hg(lit.)
• Flash Point: 216 °F
• Appearance: Clear pale yellow to red-brown/Liquid
• Density: 0.957 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0525mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.78±0.10(Predicted)
• CAS DataBase Reference: 2-tert-Butylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-tert-Butylaniline(6310-21-0)
• EPA Substance Registry System: 2-tert-Butylaniline(6310-21-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 6310-21-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-tert-Butylaniline is used as a key intermediate in the synthesis of various organic compounds. It serves as a building block for the preparation of complex molecules with specific properties and functions.
Used in the Preparation of 2,3-bis(2-tert-butyl-phenyl-imino)butane:
2-tert-Butylaniline is used as a starting material for the preparation of 2,3-bis(2-tert-butyl-phenyl-imino)butane, a compound with potential applications in materials science and chemical research.
Used in the Preparation of N,N′-bis-(2-tert-butylphenyl)naphthalene-1,4,5,8-tetracarboxylic diimides:
2-tert-Butylaniline is used in the synthesis of two rotamers, antiand syn-N,N′-bis-(2-tert-butylphenyl)naphthalene-1,4,5,8-tetracarboxylic diimides. These compounds have been investigated for their guest inclusion abilities, which can be relevant in supramolecular chemistry and the development of new materials with specific host-guest interactions.

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

Upstream product

• 1886-57-3 1-tert-butyl-2-nitrobenzene 
• 62-53-3 aniline 
• 115-11-7 isobutene 
• 253185-03-4 tert-butylbenzene 
• 75-28-5 Isobutane 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 7647-01-0 hydrogenchloride 
• 6310-20-9 4-Amino-2-nitro-tert-butylbenzene hydrochloride 
• 71-43-2 benzene 
• 3282-56-2 4-tert-butylnitrobenzene 
• 31951-12-9 4-tert-butyl-3-nitro-phenylamine 
• 4160-54-7 1-tert-butyl-2,4-dinitrobenzene 
• 59719-78-7 4-tert-butyl-3-nitrobenzoic acid 

Downstream Products

• 99858-67-0 N-(2-(tert-butyl)phenyl)formamide 
• 62171-59-9 1-(tert-butyl)-2-iodobenzene 
• 1728-46-7 2-tert-butylcyclohexanone 
• 38510-79-1 rac-6-tert-butylcyclohex-2-enone 
• 109932-97-0 (2-tert-butyl-phenyl)-methylamine 
• 103392-84-3 2-tert-Butyl-5-nitro-phenylamine 
• 105401-87-4 (2-tert-butyl-phenylsulfanyl)-acetic acid 
• 7402-70-2 N-(2-tert-butylphenyl)acetamide 
• 59238-67-4 N-(2-(tert-butyl)phenyl)benzamide 
• 32767-57-0 N-(2-tert-butyl-phenyl)-N'-phenyl-thiourea 
• 60530-65-6 N,N′-bis(4-tert-butylphenyl)formamidine 
• 17900-75-3 chloro-acetic acid-(2-tert-butyl-anilide) 
• 22025-87-2 o-tert-butyl-N,N-dimethylaniline 
• 111089-32-8 3-hydroxy-[2]naphthoic acid-(2-tert-butyl-anilide) 

Relevant articles and documents

Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines

Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.

Tertiary butylation of aniline over nanosized zeolite beta catalyst

In the current paper, we report nanosized zeolite beta to be a robust and potent catalyst for tertbutylation of aniline. Nanocrystals of beta zeolite having spherical morphology were prepared via a one-pot strategy that is based on vacuum-concentration coupled hydrothermal method. The catalyst could be used in the as-synthesized form, without any further modifications. In the presence of the as-prepared catalyst, liquid-phase tert-butylation of aniline using tert-butanol as alkylating agent proceeded successfully. Reaction parameters like duration of reaction, temperature, mole ratio of substrates and quantity of catalyst were optimized. Time-dependent data obtained was subjected to kinetic studies. Detailed studies on product selectivity were conducted. The catalyst could selectively direct the formation of C–C bonds and no N-alkylated products were detected. It also demonstrated good selectivity towards mono-substitution. The catalyst could be recovered by a simple work-up plan and could then be re-used. No appreciable loss in activity was detected in consecutive runs. Thus, the nanosized beta mediated route to introduce tert-butyl group on aniline ring can be an environment-friendly alternative to the use of homogeneous catalysts.

Synthesis method of 4,4-diamino 3,3-di-tert-butyl diphenylmethane

The invention aims at providing a synthesis method of 4,4-diamino 3,3-di-tert-butyl diphenylmethane. According to the process, o-tert-butyl aniline is used as raw materials to perform further a condensation reaction with formaldehyde under the effect of solid acid catalysts to obtain the 4,4-diamino 3,3-di-tert-butyl diphenylmethane. The reaction temperature is 90 to 150 DEG C; the reaction time is 1 to 8 hours. The o-tert-butyl aniline can be obtained through methyl tertiary butyl ether or tert-butyl alcohol alkylation reaction via aniline; the raw material cost is greatly reduced; the huge possibility is provided for the industrial application of the 4,4-diamino 3,3-di-tert-butyl diphenylmethane. The catalyst is montmorillonoid or kaolin with layered structures sold in the market. The catalyst can be cyclically used. High activity is realized on the synthesis of 4,4-diamino 3,3-di-tert-butyl diphenylmethane from the o-tert-butyl and the formaldehyde. The process belongs to a green environment-friendly and efficient synthesis process for the 4,4-diamino 3,3-di-tert-butyl diphenylmethane.

Catalytic transfer reductive cleavage of azo compounds to amines using chitosan-supported formate and zinc

A convenient method for the cleavage of azo derivatives to the corresponding amines using chitosan-supported formate as hydrogen donors in conjunction with zinc is described.

Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source

Rhodium(II) dicarboxylate complexes were discovered to catalyze the intramolecular amination of unactivated primary, secondary, or tertiary aliphatic C-H bonds using aryl azides as the N-atom precursor. While a strong electron-withdrawing group on the nitrogen atom is typically required to achieve this reaction, we found that both electron-rich and electron-poor aryl azides are efficient sources for the metal nitrene reactive intermediate.

Highly selective amination of o-and p-alkyl phenols over Pd/Al 2O3-BaO

A series of Pd-based catalysts were prepared and examined for the amination of 2,6-dimethylphenol in a fixedbed reactor. The best results were obtained for Pd/Al2O3-BaO with a conversion of 99.89% and a selectivity of 91.16%. These catalysts were characterized using BET, XRD, XPS, TEM and NH3-TPD. Doped BaO not only improved the dispersion of the Pd particles but also decreased the acidity of the catalyst, which remarkably enhanced the selectivity and stability of the catalyst. The generality of Pd/Al 2O3-BaO for this kind of reaction was demonstrated by catalytic aminations of o- and p-alkyl phenols.

A novel naphthylmethyleneimino-type photocleavable protecting group for primary amines

A novel naphthylmethyleneimino-type protecting group for aliphatic and aromatic primary amines including α-amino acids was devised and its introduction was accomplished in good to excellent yields. This type of protecting group was found to be cleanly removed photochemically to regenerate the primary amines in good to high yields, regardless of steric and electronic properties. Georg Thieme Verlag Stuttgart.

Para-alkylation of aromatic primary amines

A method is provided for producing primarily para alkyl aromatic amines by alkylating a primary aromatic amine with an olefin in the presence of an acid activated clay.

Synthesis of functionalized carbamates through a palladium-catalyzed reductive carbonylation of substituted nitrobenzenes

The palladium-catalyzed reductive carbonylation of ortho and para-substituted nitrobenzenes has proven to be an attractive route for the synthesis of functionalized carbamates. For the Pd(1,10-phenanthroline)2(triilate}2 catalyst system, the scope of the reaction has been studied. Substrates with electron-donating substituents at the para position were found to decrease the catalytic activity, most probably as a result of their relatively low oxidizing capacity. The selectivity towards the desired carbamate, however, was increased for these substrates. Under the influence of electron-withdrawing substituents the azoxybenzene and azobenzene derivatives became important side products. Introduction of large steric hindrance at the ortho position of the nitro substrates gave rise to an interesting side reaction, viz. methoxylation of the aromatic ring. The methoxylation reaction appeared to occur on an intermediate species in the catalytic cycle. Several functionalities have shown to be resistant to the reaction conditions required for the conversion of the nitro group. Especially with 4-nitrobenzoic acid, an extremely high activity and selectivity was found, thus yielding a very convenient synthesis for N-protected amines containing carboxylic acid functions. VCH Verlagsgesellschaft mbH.

Para-bromination of ortho-alkyl anilines

A process of selectively preparing p-bromo-o-alkylanilines (e.g. 4-bromo-2-methylaniline) by reacting o-alkylanilines (e.g., 2-methylaniline) with unadsorbed bromine in a solvent selected from the group consisting of an inert di- tri- or tetrahaloaliphatic hydrocarbon (e.g., dichloromethane and dibromomethane), an alkyl nitrile (e.g., acetonitrile) and mixtures thereof.