4747-21-1

Usage

Uses

Used in Pharmaceutical Industry:
N-Isopropylmethylamine is used as a reagent in the synthesis of novel 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]-tryptamines and their [α,α,β,β,β-D4]-counterparts following the Speeter and Anthony procedure. These synthesized compounds have potential applications in the development of new pharmaceuticals.
Used in Chemical Industry:
N-Isopropylmethylamine is used in the generation of in situ micelles with distinct sizes, by sequential self-assembly of a series of stimuli-responsive amphiphilic block copolymers, prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. This process allows for the creation of micelles with specific properties, which can be useful in various chemical applications, such as drug delivery and nanotechnology.

Flammability and Explosibility

Highlyflammable

InChI:InChI=1/C4H11N/c1-4(2)5-3/h4-5H,1-3H3

Upstream product

• 110-86-1 pyridine 
• 996-35-0 N,N-dimethylisopropyl amine 
• 94-36-0 dibenzoyl peroxide 
• 75-52-5 nitromethane 
• 67-64-1 acetone 
• 74-89-5 methylamine 
• 75-26-3 isopropyl bromide 
• 5339-69-5 N-isopropylbenzenesulfonamide 
• 74-88-4 methyl iodide 
• 103-67-3 benzyl-methyl-amine 
• 6852-56-8 N-benzylideneisopropylamine 
• 77-78-1 dimethyl sulfate 
• 10556-98-6 1,3,5-Triisopropyl-1,3,5-triazacyclohexane 
• 91076-68-5 mono-trimethylsilylphosphite 

Downstream Products

• 2893-49-4 N-methyl-N-isopropylaminoethyl alcohol 
• 25244-11-5 2-(isopropyl-methyl-amino)-1-phenyl-ethanol 
• 860572-38-9 N-isopropyl-N-methyl-β-alanine ethyl ester 
• 6712-59-0 5-(4-chloro-phenyl)-1-isopropyl-1-methyl-biguanide 
• 30533-08-5 N-methyl-N-nitroso-2-propanamine 
• 63299-59-2 O-(2,6-Dimethylphenyl)-N-isopropyl-N-methyl-(thiocarbamat) 
• 52317-75-6 3-(2,4-Dimethyl-phenyl)-1-isopropyl-1-methyl-thiourea 
• 52317-82-5 3-(4-Bromo-2-methyl-phenyl)-1-isopropyl-1-methyl-thiourea 
• 38128-77-7 Rifamycin-B- 
• 64796-57-2 3-[1-(3-Chloro-phenyl)-1-methyl-ethyl]-1-isopropyl-1-methyl-urea 
• 64796-85-6 3-[1-(4-Chloro-phenyl)-1-methyl-ethyl]-1-isopropyl-1-methyl-urea 
• 5756-49-0 N-Methyl-N-isopropyl-N-pentyl-amin 
• 54966-01-7 N-Methyl-N-isopropyl-butyramid 
• 23580-89-4 methyl-(3-phenyl-propyl)-amine 

Relevant academic research and scientific papers

Spectral and mechanistic investigations of ruthenium(III) catalyzed oxidation of atenolol by diperiodatocuprate(III) in aqueous alkaline medium 1

The kinetics of ruthenium(III) catalyzed oxidation of atenolol by diperiodatocuprate(III) in aqueous alkaline medium at a constant ionic strength of I = 0.10 M has been studied spectrophotometrically at 27°C. The reaction between diperiodatocuprate(III) and atenolol in alkaline medium in presence of ruthenium(III) exhibits 2: 1 stoichiometry (atenolol: diperiodatocuprate(III)). The main products were identified by spot test, IR, NMR, and LC-MS. The reaction is of first order in DPC concentrations and has less than unit order in both ATN and alkali concentrations. The order in ruthenium(III) was unity. Intervention of free radicals was observed in the reaction. Increase in periodate concentration decreases the rate. The oxidation reaction in alkaline medium has been shown to proceed via a ruthenium(III)-atenolol complex, which reacts with monoperiodatocuprate(III) in a rate determining step followed by other fast steps to give the products. Probable mechanism is proposed and discussed. The activation parameters with respect to the slow step of the mechanism and thermodynamic quantities were determined and discussed. Pleiades Publishing, Ltd., 2012.

Reviving electrocatalytic reductive amination: A sustainable route from biogenic levulinic acid to 1,5-dimethyl-2-pyrrolidone

The electrocatalytic reductive amination offers a green pathway to N-containing platform and fine chemicals by using water as a hydrogen source and benign reaction conditions. However, systematic studies about suitable reaction conditions and application to biogenic substrates are rare. Here, we present the electrochemical transformation of levulinic acid to 1,5-dimethyl-2-pyrrolidone. Data from Smirnov et al. for the amination of conventional ketones were validated and extended by systematically investigating the impact of electrode material, substrate concentration, current density, solvent, electrolyte, and pH value. High substrate concentrations in an aqueous electrolyte with a high pH value enable imine formation and copper is identified as the most selective cathode material at current densities lower than 40 mA cm-2. The application of optimized reaction conditions to levulinic acid, followed by a short heating procedure for dehydrative ring closure, led to 1,5-dimethyl-2-pyrrolidone in 78% yield. The systematic approach of this work presents the first example of an electrochemical levulinic acid amination and provides a methodology for the benign synthesis of other N-containing species. This journal is

Synthesis method of N-methylisopropylamine

The invention relates to the field of preparation of pesticide and medical intermediates, in particular to a preparation method of N-methylisopropylamine. The method comprises the following steps: taking isopropylamine as a raw material, taking dimethyl carbonate as a reaction solvent, and carrying out heat preservation reaction under the catalysis of a basic catalyst; and after the reaction is finished, filtering to remove the catalyst, carrying out rectification separation on filtrate, and separating the solvent dimethyl carbonate from the product. The method effectively controls the generation of a byproduct disubstituted N, N-dimethyl isopropylamine, and effectively controls the conversion rate and selectivity of raw materials, and compared with the prior art, the novel synthesis method of N-methyl isopropylamine has the following effective effects: the raw materials are easy to obtain, the reaction is mild, the reaction steps are simple, the cost of the raw materials is lower, the selected solvent dimethyl carbonate is relatively low in toxicity and can be recycled, so that the product is a green chemical product with a development prospect, and the method is extremely low in three-waste amount and relatively great in industrial application prospect.

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.

Ligand-controlled α- And β-arylation of acyclic N-boc amines

The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.

METHOD FOR THE CONTINUOUS PRODUCTION OF AN AMINE

The invention relates to a method for the continuous production of an amine by reacting a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound, selected from the group including ammonia, primary and secondary amines, at a temperature in the range of from 80 to 350 °C in the presence of a zirconium dioxide-containing catalyst, the catalytically active weight of the catalyst prior to its reduction with hydrogen containing 90 to 99.8 % by weight of zirconium dioxide (ZrO2), 0.1 to 5.0 % by weight of oxygen-containing compounds of palladium and 0.1 to 5.0 % by weight of oxygen-containing compounds of platinum.

Kinetic and mechanistic investigation of oxidative degradation and deamination of atenolol by diperiodatonickelate(IV) in aqueous alkaline medium

The kinetics of oxidation of atenolol by diperiodatonickelate(IV) (DPN) in aqueous alkaline medium at a constant ionic strength of 1.0 mol dm-3 was studied spectrophotometrically. The reaction is first order in [DPN], less than unit order in [alkali] and zero order in [ATN]. Addition of periodate has no effect on the reaction. Effect of added products, ionic strength and dielectric constant of the reaction medium have been investigated. The main products were identified by I.R., N.M.R., fluorimetry and mass spectral studies. A mechanism involving the deprotonated diperiodatonickelate (IV) (DPN) as the reactive species of the oxidant has been proposed. The reaction constants involved in the different steps of mechanism are calculated. The thermodynamic activation parameters with respect to the slow step of the mechanism are computed and discussed.

Electrochemical oxidation of N-p-toluenesulfinamides

Matrix presented Contrasting and interesting electrochemical behavior is observed in anodic oxidation of N-substituted p-toluenesulfinamides under controlled current conditions. For sulfinamides derived from secondary alkylamines and primary arylamines, the N-sulfinyl group is removed and the corresponding amines are formed; for sulfinamides derived from primary alkylamines, sulfur oxidation yields the corresponding sulfonamides in good yields.

Preparation process of aminoacetamide derivative

Disclosed herein are novel processes for preparing aminoacetamide derivatives, wherein: (1) a secondary amine is reacted with a 2-haloacetamide in the presence or absence of at least one solvent selected from water, lower alcohols, aromatic solvents and acetic acid esters; (2) an N-benzylideneamine derivative is reacted with dimethyl sulfate or diethyl sulfate to form a secondary amine, and this secondary amine is then reacted with a 2-haloacetamide; and (3) a primary amine is reacted with benzaldehyde to form an N-benzylideneamine derivative, this product is then reacted with dimethyl sulfate or diethyl sulfate to form a secondary amine, and this secondary amine is further reacted with a 2-haloacetamide. The 2-aminoacetamide derivatives are useful as intermediates for the preparation of novel antibiotics.

Stereodynamics of N-Ethyl-N-methyl-2-aminopropane. 1H and 13C DNMR Studies. Molecular Mechanics Calculations

N-Ethyl-N-methyl-2-aminopropane (EMAP) is one of the simplest tertiary aliphatic amines that has a chiral center at nitrogen.Racemization occurs by inversion-rotation at the pyramidal nitrogen.For each EMAP enantiomer, additional conformational interconversions occur via isolated rotation about carbon-nitrogen bonds.The 1H and 13C dynamic NMR (DNMR) spectra of EMAP and a selectively deuterated derivative decoalesce into four subspectra at 95 K.The spectrum at 95 K is best rationalized in terms of five equilibrium conformations present at concentrations high enough to be NMR-detectable including two conformations that interchange rapidly even at 95 K.A two-letter designation is used to name the various conformations.The first letter defines the orientation of the ethyl methyl group (G denotes gauche to the lone pair and to the N-methyl group; G' denotes gauche to the lone pair and to the isopropyl group; A denotes anti to the lone pair).The second letter defines the orientation of the isopropyl methine proton (G denotes gauche to the lone pair and to the N-methyl group; G' denotes gauche to the lone pair and to the ethyl group; A denotes anti to the lone pair).The major subspectrum at 95 K is assigned to a family of G'G' and GG' conformations (59percent) that interconvert rapidly at 95 K.The other three subspectra are assigned to the GG (34percent), AA (5percent), and GA (2percent) conformations.Simulations of the DNMR spectra reveal a barrier to inversion-rotation at nitrogen (ΔG(excit.) = 7.5 kcal/mol at 160 K) that is higher than the barriers for a number of observable isolated rotations about the N-CH2 and N-CH bonds (ΔG(excit.) = 4.7-6.4 kcal/mol).A 5000-point optimized energy surface computed as a function of two dihedral angles by using Allinger's MM2(87) computer program, MM2(87) energy calculations for all the optimized equilibrium conformations of EMAP, and MM2(87)-calculated isolated rotation barriers show excellent agrreement with the DNMR data.