6068-69-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 1841, 1971 DOI: 10.1021/jo00812a030

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

Upstream product

• 98-95-3 nitrobenzene 
• 78-93-3 butanone 
• 78-86-4 s-butyl chloride 
• 62-53-3 aniline 
• 78-76-2 s-butyl bromide 
• 78-92-2 iso-butanol 
• 513-48-4 2-butyl iodide 
• 33966-50-6 SEC-BUTYLAMINE 
• 108-90-7 chlorobenzene 
• 52615-84-6 N-chloro-sec-butylamine 
• 100-58-3 phenylmagnesium bromide 
• 3262-89-3 triphenylboroxine 
• 145279-67-0 O-benzoyl-N-sec-butylhydroxylamine 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 101289-90-1 N-sec-butyl-N-nitroso-4-phenylazo-aniline 
• 84695-43-2 1-(1-methylpropyl)-1-phenylhydrazine 
• 67651-62-1 N-sec-Butyl-N-alkyl-3,4-dichlorbenzamid 
• 72411-06-4 1-sec-Butyl-1-phenyl-3-phenylacetyl-thiourea 
• 55239-86-6 C₁₁H₁₄ClNO 
• 101582-56-3 N-sec-butyl-toluene-4-sulfonanilide 
• 32797-02-7 N-sec-butyl-N-nitroso-aniline 
• 25012-18-4 2-(N-sec-butyl-anilino)-ethanol 

Relevant academic research and scientific papers

Titanium-Catalyzed Hydroaminoalkylation of Ethylene

The first examples of titanium-catalyzed hydroaminoalkylation reactions of ethylene with secondary amines are presented. The reactions can be achieved with various titanium catalysts and they do not require the use of high pressure equipment. In addition, the first solid-state structure of a titanapyrrolidine that is formed by insertion of an alkene into the Ti?C bond of a titanaaziridine is reported.

A Highly Active PN3 Manganese Pincer Complex Performing N-Alkylation of Amines under Mild Conditions

A highly active Mn(I) catalyst based on a nonsymmetric PN3-ligand scaffold for the N-alkylation of amines with alcohols utilizing the borrowing hydrogen methodology is reported. A broad range of anilines and the more challenging aliphatic amines were alkylated with primary and secondary alcohols. Moreover, the combination of low catalyst loadings and mild reaction conditions provides high efficiency for this atom-economic transformation.

Practical and regioselective amination of arenes using alkyl amines

The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.

N-Alkylation of Aniline and Its Derivatives by Alcohols in the Presence of Copper Compounds

N-Alkyl- and N,N-dialkyl-substituted anilines were obtained in the reaction of aniline and its derivatives with primary and secondary alcohols in the presence of catalysts CuCl2·2H2O, CuBr2 and halomethanes as promoters.

Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides without inert gas protection

A solvent-free Buchwald-Hartwig amination had been developed under high-speed ball-milling conditions, which afforded the desired products with moderate to high yields. The addition of sodium sulfate was found to be crucial for improving both the performance and the reproducibility. Comparative solvent-free stirring experiments implicated the importance of mechanical interaction for the transformation, and the inert gas was proved to be unnecessary for this amination.

Electrophilic Amination with Nitroarenes

An exceptionally general electrophilic amination, which directly transforms commercially available nitroarenes into alkylated aromatic aminoboranes with zinc organyl compounds was developed. The reaction starts with a two-step partial reduction of the nitro group to a nitrenoid, which is used in situ as the electrophilic amination reagent. To facilitate isolation, the resulting air- and moisture-sensitive aminoboranes were reacted with a range of electrophiles. The method not only represents a direct transformation of nitro compounds into electrophilic amination reagents but also provides an elegant alternative to dehydrocoupling methods for the generation of aminoboranes.

AQUEOUS RESIN BASED INKJET INKS

An inkjet ink includes a) an aqueous medium; and b) capsules composed of a polymeric shell surrounding a core; wherein the capsules are dispersed in the aqueous medium using a dispersing group covalently bonded to the polymeric shell; the core contains on

Cu2O/nano-CuFe2O4: An efficient and magnetically recoverable catalyst for the ligand-free N-arylation of amines and nitrogen heterocycles with aryl halides

An efficient strategy has been developed for the N-arylation of azoles and aliphatic amines with aryl halide using a Cu2O/nano-CuFe2O4 magnetic composite as the catalyst and KOH as the base. The methodology is found to be applicable to a variety of nitrogen-containing heterocycles, such as imidazole, indole, and pyrrole, as well as aliphatic amines in high yields with practical simplicity under cost-effective "ligand-free" conditions. The magnetic property of the catalyst allowed its fast separation from the reaction medium by an external magnet. Additionally, the inexpensive catalyst could be recycled for five consecutive runs with small drops in catalytic activity.

Magnetic nanoparticle-supported phosphine gold(i) complex: A highly efficient and recyclable catalyst for the direct reductive amination of aldehydes and ketones

The direct reductive amination of aldehydes and ketones has been achieved in dichloromethane at room temperature by using a magnetic nanoparticle-supported phosphine gold(i) complex [Fe3O4@SiO2-P-AuCl] as the catalyst and ethyl Hantzsch ester as the hydrogen source, yielding a variety of secondary amines in excellent yields under neutral conditions. The new heterogeneous gold catalyst can be prepared by a simple procedure from commercially readily available reagents and can easily be separated from the reaction mixture by applying an external magnet and recycled at least 10 times without any loss of activity.

Cobalt-Catalyzed Synthesis of Aromatic, Aliphatic, and Cyclic Secondary Amines via a "hydrogen-Borrowing" Strategy

The replacement of precious metals with inexpensive, less toxic, and earth-abundant elements in typical noble-metal-mediated organic transformations is a major goal in current synthetic chemistry and industries. The metal-catalyzed N-alkylation of amines with other amines through a "hydrogen-borrowing" principle represents a green and atom-economical reaction for the synthesis of secondary amines. However, catalysts developed thus far that are effective for this process remain quite scarce and are only limited to a few ruthenium and iridium complexes. In this work, we present a cobalt-catalyzed selective alkylation of amines with amines to synthesize a large variety of secondary amines. A range of amine substrates have been converted to the corresponding products through hetero- or homocoupling between amines. Cyclic sec-amines are also achieved from diamine precursors as rare examples.