91-67-8

Usage

Chemical Properties

CLEAR PALE YELLOW TO ORANGE-BROWN LIQUID

InChI:InChI=1/C11H17N/c1-4-12(5-2)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 638-03-9 m-toluidine hydrochloride 
• 64-67-5 diethyl sulfate 
• 108-44-1 1-amino-3-methylbenzene 
• 591-17-3 meta-bromotoluene 
• 109-89-7 diethylamine 
• 106-38-7 para-bromotoluene 
• 95-46-5 2-methylphenyl bromide 
• 1066-87-1 (N,N-diethylamino)tributyltin 
• 352-70-5 m-Fluorotoluene 
• 75-36-5 acetyl chloride 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 108-88-3 toluene 
• 4913-13-7 3,5,N,N-tetramethylaniline 

Downstream Products

• 31538-83-7 Diethyl-(3-methyl-4-p-tolylazo-phenyl)-amine 
• 70895-80-6 bis<4-(N,N-diethylamino)-2-methylphenyl>(4-methylphenyl)methane 
• 69432-33-3 C₃₄H₄₀N₈ 
• 116884-79-8 3-Bromo-2-(4-diethylamino-2-methyl-phenyl)-1,1-dioxo-1H-1λ⁶-thiochromen-4-one 
• 4913-13-7 3,5,N,N-tetramethylaniline 
• 2217-07-4 N,N-dipropylaniline 
• 5022-99-1 7-(4-Diaethylamino-2-methyl-phenyl)-1,3,5-cycloheptatrien 
• 92-14-8 4-[N,N-bis(ethyl)amino]-2-methylbenzaldehyde 
• 52177-26-1 N,N-diethyl-3-methyl-4-nitrobenzenamine 

Relevant academic research and scientific papers

Hydrogenation and: N-Alkylation of anilines and imines via transfer hydrogenation with homogeneous nickel compounds

The nickel-catalyzed N-Alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the CN bond reduction and N-Alkylation of a variety of imines with ethanol, the latter acting as a hydrogen and acetaldehyde source, which allowed for the reduction and subsequent condensation to yield the corresponding N-Alkylated products.

Photochemical Cleavage of Benzylic C-N Bond to Release Amines

The 3-(diethylamino)benzyl (DEABn) group has been studied for releasing primary, secondary, and tertiary amines by direct photochemical breaking of the benzylic C-N bond. While photochemical release of primary and secondary amines provides high yields in

Homogeneous catalytic hydrogenation of amides to amines

Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4-pentanedione), triphos [1,1,1-tris- (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and the mechanism of the reaction, a range of methanesulfonato complexes has been prepared from prepared from [Ru(acac) 3], triphos and MSA, or from reactions of [RuX-(OAc)(triphos)] (X=H or OAc) or [RuH2(CO)(triphos)] with MSA. Crys-tallographically characterised complexes include: [Ru(OAc-κ1O) 2(H2O)-(triphos)], [Ru(OAc-κ2O,O') (CH3SO3-κ1O)(triphos)], [Ru(CH 3SO3-κ1O)2-(H 2O)(triphos)] and [Ru2(μ-CH3SO 3)3-(triphos)2][CH3SO3], whereas other complexes, such as [Ru(OAc-κ1O)(OAc- κ2O,O')(triphos)],[Ru(CH3SO3- κ1O)(CH3SO3-κ2O,O')- (triphos)], H[Ru(CH3SO3-κ1O) 3-(triphos)], [RuH(CH3SO3-κ1O) (CO)-(triphos)] and [RuH(CH3SO3-k2O,O')- (triphos)] have been characterised spectroscopically. The interactions between these various complexes and their relevance to the catalytic reactions are discussed.

One-pot photo-reductive N-alkylation of aniline and nitroarene derivatives with primary alcohols over Au-TiO2

We report the photo-catalytic N-alkylation of aniline by Au-TiO 2. We successfully alkylate aniline with several primary alcohols. The combined selectivities of mono- and di-alkylated products were always in excess of 70% and dependent on the alkylating alcohol used. A one-pot reaction from nitrobenzene was found to be possible with several substrates. Preliminary experiments showed that this approach could be adopted for the production of lactams using terminal amino-alcohols. The Royal Society of Chemistry 2013.

C(sp3)-F bond activation of CF3-substituted anilines with catalytically generated silicon cations: Spectroscopic evidence for a hydride-bridged Ru-S dimer in the catalytic cycle

Heterolytic splitting of the Si-H bond mediated by a Ru-S bond forms a sulfur-stabilized silicon cation that is sufficiently electrophilic to abstract fluoride from CF3 groups attached to selected anilines. The ability of the Ru-H complex, generated in the cooperative activation step, to intramolecularly transfer its hydride to the intermediate carbenium ion (stabilized in the form of a cationic thioether complex) is markedly dependent on the electronic nature of its phosphine ligand. An electron-deficient phosphine thwarts the reduction step but, based on the Ru-S catalyst, half of an equivalent of an added alkoxide not only facilitates but also accelerates the catalysis. The intriguing effect is rationalized by the formation of a hydride-bridged Ru-S dimer that was detected by 1H NMR spectroscopy. A refined catalytic cycle is proposed.

CuI/DMPAO-catalyzed N-arylation of acyclic secondary amines

DMPAO has been found to be a powerful ligand to enable copper-catalyzed coupling of aryl halides with aliphatic acyclic secondary amines take place under relatively mild conditions, and coupling of aryl halides with primary amines and cyclic secondary amines proceeds at low catalyst loading.

Cu(ii)-catalyzed C-H (SP3) oxidation and C-N cleavage: Base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source

Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl2, with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.

METHOD AND DEVICE FOR PRODUCING AROMATIC AMINES BY HETEROGENEOUS CATALYZED HYDRATION

The present invention relates to a process and an apparatus for preparing aromatic amines by means of a heterogeneously catalysed hydrogenation, wherein the catalyst required for the reaction is applied to the interior wall of one or more reaction channel

An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide

It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives. Copyright

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.