35161-70-7

Usage

Uses

Used in Chemical Synthesis:
N-METHYLHEXYLAMINE is used as a building block in the synthesis of dialkyldithiocarbamato cadmium complexes Cd[S2CNRR′]2. These complexes have potential applications in various fields, such as agriculture, pharmaceuticals, and materials science.
Used in Pharmaceutical Industry:
N-METHYLHEXYLAMINE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs and medications.
Used in Agriculture:
N-METHYLHEXYLAMINE is used in the synthesis of dialkyldithiocarbamato cadmium complexes, which have potential applications in agriculture as pesticides or fungicides. These complexes can help protect crops from pests and diseases, ensuring a healthy and productive harvest.
Used in Materials Science:
The dialkyldithiocarbamato cadmium complexes synthesized using N-METHYLHEXYLAMINE have potential applications in materials science. These complexes can be used to develop new materials with unique properties, such as improved conductivity, stability, or catalytic activity.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 3038, 1973 DOI: 10.1021/ja00790a064Tetrahedron Letters, 26, p. 1153, 1985 DOI: 10.1016/S0040-4039(00)98420-XSynthetic Communications, 20, p. 231, 1990 DOI: 10.1080/00397919008052288

InChI:InChI=1/C7H17N/c1-3-4-5-6-7-8-2/h8H,3-7H2,1-2H3

Upstream product

• 544-10-5 1-Chlorohexane 
• 74-89-5 methylamine 
• 111-25-1 1-bromo-hexane 
• 111-26-2 hexan-1-amine 
• 100-61-8 N-methylaniline 
• 6154-14-9 N-chloromethylamine 
• 127146-31-0 1-hexyl-dimethylborane 
• 66-25-1 hexanal 
• 1072-44-2 N-methylaziridine 
• 77-78-1 dimethyl sulfate 
• 142-61-0 Hexanoyl chloride 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 62316-73-8 N-hexyl-P,P-diphenylphosphinic amide 

Downstream Products

• 89530-00-7 C₁₄H₂₂N₄O 
• 4385-04-0 N,N-dimethylhexylamine 
• 37615-53-5 N,N-dihexyl-N-methylamine 
• 74109-24-3 C₁₄H₂₁N₃O₂ 
• 58965-42-7 N-hexyl-N-methylcarbamoyl chloride 
• 69-72-7 salicylic acid 
• 742698-71-1 4-[(hexyl-methyl-amino)-methyl]-benzoic acid methyl ester 
• 1207717-23-4 N-hexyl-N-methyl-4-methylaniline 
• 6378-65-0 n-hexyl caproate 
• 1346845-86-0 N-hexyl-N-methylhexanamide 
• 1421671-37-5 C₂₈H₄₂N₂S₄Sn 
• 1562031-12-2 4-hydroxy-N-α-tert-butoxycarbonyl-D-phenylglycine N-hexylmethylamide 
• 1438886-25-9 N-hexyl-4-methyl-N-(2-phenylpropyl)benzenesulfonamide 
• 1438886-27-1 N-hexyl-4-methyl-N-(3-phenylpropyl)benzenesulfonamide 

Relevant academic research and scientific papers

Green and chemo selective amine methylation using methanol by an organometallic ruthenium complex

Herein a green and convenient catalytic N-methylation of aniline and n-hexylamine using methanol as a dual methylation agent and solvent has been investigated. A new ruthenium carbonyl complex was synthesized and applied as a homogeneous catalyst in methylation reaction. The solid-state structure of the complex was determined by X-ray crystallographic analysis which indicate xantphos ligand bonded to ruthenium (II) as a tridentate pincer ligand by two P donor and one O atom. The catalytic system showed excellent conversion and selectivity toward N-methylaniline, and N,N-hexyldimethylamine at 140°C.

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Mechanistic Insight into the Catalytic Promiscuity of Amine Dehydrogenases: Asymmetric Synthesis of Secondary and Primary Amines

Biocatalytic asymmetric amination of ketones, by using amine dehydrogenases (AmDHs) or transaminases, is an efficient method for the synthesis of α-chiral primary amines. A major challenge is to extend amination to the synthesis of secondary and tertiary amines. Herein, for the first time, it is shown that AmDHs are capable of accepting other amine donors, thus giving access to enantioenriched secondary amines with conversions up to 43 %. Surprisingly, in several cases, the promiscuous formation of enantiopure primary amines, along with the expected secondary amines, was observed. By conducting practical laboratory experiments and computational experiments, it is proposed that the promiscuous formation of primary amines along with secondary amines is due to an unprecedented nicotinamide (NAD)-dependent formal transamination catalysed by AmDHs. In nature, this type of mechanism is commonly performed by pyridoxal 5′-phosphate aminotransferase and not by dehydrogenases. Finally, a catalytic pathway that rationalises the promiscuous NAD-dependent formal transamination activity and explains the formation of the observed mixture of products is proposed. This work increases the understanding of the catalytic mechanism of NAD-dependent aminating enzymes, such as AmDHs, and will aid further research into the rational engineering of oxidoreductases for the synthesis of α-chiral secondary and tertiary amines.

Synthesis of β-Chiral Amines by Dynamic Kinetic Resolution of α-Branched Aldehydes Applying Imine Reductases

Imine reductases (IREDs) allow the one-step preparation of optically active secondary and tertiary amines by reductive amination of ketones. Until now, mainly α-chiral amines have been prepared by this route. In this study, we explored the possibility of synthesizing β-chiral amines, a class of compounds which is also frequently found as structural motif in pharmaceuticals but much more challenging to prepare due to the following reasons: (i) The aldehyde substrate already contains the chiral center and needs to be racemized to enable full conversion. (ii) Because the intermediate imine bears the stereo center two carbon atoms remote to the imine nitrogen, it is more challenging to achieve high enantioselectivity compared to α-chiral amine synthesis. For investigating the proof of concept, we first confirmed that different IREDs are able to convert a variety of α-branched aldehydes when combined with five different amine substrates. The IRED from Streptomyces ipomoeae was a suitable enzyme facilitating the dynamic kinetic resolution of 2-phenylpropanal and a substituted 2-methyl-3-phenylpropanal: the corresponding N-methylated β-chiral amines were obtained with '95 % conversion and 78 and 95 %ee. Other amines were formed with low to moderate enantiomeric excess. This exemplifies the potential of IREDs for the one-step synthesis of secondary β-chiral amines, but also the challenge to identify highly selective enzymes for a desired amine product.

Method for selectively preparing N-monomethylamine compound

The invention discloses a method for selectively preparing an N-monomethylamine compound. The method takes an amine compound, formaldehyde and H2 as reaction raw materials; the raw materials react in a reaction medium in the presence of a compound catalyst at 30 DEG C-180 DEG C for 2h-48h, so as to obtain the N-monomethylamine compound; and the compound catalyst is composed of oxides of at least two of the following metal or oxides of least one of the following metal and at least one metal simple substance: aluminum, copper, nickel, cobalt and iron. According to the method for preparing the N-monomethylamine compound, the conversion ratio and the selectivity of N-monomethylamine are relatively high; the H2 is used as a reducing agent and is clean, cheap and environment-friendly; the catalyst utilized by the method is cheap, simple to prepare and high in catalysis efficiency; and the method has mild preparation and reaction conditions and the catalyst has no corrosiveness, is easy to separate and can be repeatedly used.

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

METHOD OF FORMING CARBONYL COMPOUND AND DEPROTECTION METHOD OF AMIDE-BASED COMPOUND USING A CLEAVAGE REACTION OF CARBON-NITROGEN BOND

The present invention relates to a preparation method of a carbonyl compound and a method for removing nitrogen-end protective group of an amide-based compound. The carbonyl compound is prepared by having a photocatalytic reaction of an amine-based group using water and an oxidizing agent. Therefore, the preparation method can prepare a carbonyl compound by usefully cutting carbon-nitrogen bonds at mild conditions, and such cutting reaction of carbon-nitrogen bonds can be usefully used for removing a protective group combined to an amide-based compound including amide or sulfonyl amide having carbon-nitrogen bonds.COPYRIGHT KIPO 2016

Reductive amination using a combination of CaH2 and noble metal

Amines were prepared by a reductive amination reaction in the presence of calcium hydride and Pt/C. The in situ formation of water seems to be the key to activate CaH2 to reduce the intermediate imine.

Catalytic hydrogenation of amides to amines under mild conditions

Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright

Thermodynamic and nuclear magnetic resonance study of the reactions of α- and β-cyclodextrin with acids, aliphatic amines, and cyclic alcohols

Titration calorimetry was used to determine equilibrium constants and standard molar enthalpy, Gibbs energy, and entropy changes for the reactions of a series of acids, amines, and cyclic alcohols with α- and β-cyclodextrin. The results have been examined in terms of structural features in the ligands such as the number of alkyl groups, the charge number, the presence of a double bond, branching, and the presence of methyl and methoxy groups. The values of thermodynamic quantities, in particular the standard molar Gibbs energy, correlate well with the structural features in the ligands. These structural correlations can be used for the estimation of thermodynamic quantities for related reactions. Enthalpy-entropy compensation is evident when the individual classes of substances studied herein are considered, but does not hold when these various classes of ligands are considered collectively. The NMR results indicate that the mode of accommodation of the acids and amines in the α-cyclodextrin cavity is very similar, but that the 1-methyl groups in 1-methylhexylamine and in 1-methylheptylamine and the N-methyl group in N-methylhexylamine lie outside the α-cyclodextrin cavity. This latter finding is consistent with the calorimetric results. Many of the thermodynamic and NMR results can be qualitatively understood in terms of van der Waals forces and hydrophobic effects.