643-28-7

Usage

Uses

Used in Chemical Synthesis:
2-Isopropylaniline is used as a reagent in the determination of tungsten. It plays a crucial role in analytical chemistry for the detection and quantification of this important metal.
Used in Coordination Chemistry:
2-Isopropylaniline is used in the synthesis of a colorless amine-coordinated zinc complex. The study of the reactions between 1,1'-bis(hydroxymethyl)ferrocene and 2-isopropylaniline, in the presence of a catalyst [RuCl2(PPh3)3], has shown its potential in creating new coordination compounds with interesting properties.

InChI:InChI=1/C9H13N/c1-7(2)8-5-3-4-6-9(8)10/h3-7H,10H2,1-2H3

Upstream product

• 98-82-8 Isopropylbenzene 
• 6526-72-3 o-nitrocumene 
• 4375-15-9 3-methyl-2,3-dihydro-1H-indole 
• 52562-19-3 2-isopropenylaniline 
• 917-64-6 methyl magnesium iodide 
• 53165-22-3 2-(2'-aminophenyl)-1,3-dithiane 
• 74-98-6 propane 
• 62-53-3 aniline 
• 67-63-0 isopropyl alcohol 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 91-17-8 decalin 
• 7647-01-0 hydrogenchloride 
• 75-07-0 acetaldehyde 

Downstream Products

• 19246-04-9 N-(2-isopropylphenyl)acetamide 
• 93007-80-8 2-benzamido-1-isopropylbenzene 
• 101287-23-4 N-(2-isopropylphenyl)-4-methylbenzenesulfonamide 
• 55359-23-4 2-isopropyl-N,N-dimethylbenzeneamine 
• 90874-73-0 N-(2-isopropylphenyl)formamide 
• 62655-20-3 1,3-dibromo-5-isopropylbenzene 
• 120-72-9 indole 
• 88-69-7 2-(1-methylethyl)phenol 
• 19099-54-8 2-isopropyliodobenzene 
• 117146-34-6 2-(2-isopropylphenylthio)acetic acid 
• 31539-91-0 N-(2-isopropyl-4-nitrophenyl)acetamide 
• 1627-75-4 3-methyl-isoxazole-4,5-dione 4-[(2-isopropyl-phenyl)-hydrazone] 
• 35452-49-4 N-benzyl-2-isopropylaniline 
• 42022-52-6 ethyl 2-((2-isopropylphenyl)amino)-2-oxoacetate 

Relevant academic research and scientific papers

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.

Mild deprotection of the: N-tert -butyloxycarbonyl (N -Boc) group using oxalyl chloride

We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90percent. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy. This journal is

Telescoped Sequence of Exothermic and Endothermic Reactions in Multistep Flow Synthesis

A multistep sequential flow synthesis of isopropyl phenol is demonstrated, involving 4-step exothermic, endothermic, and temperature sensitive reactions such as nitration, reduction, diazotization, and high temperature hydrolysis. Nitration of cumene with fuming nitric acid produces 2- A nd 4-nitrocumene which are converted into respective cumidines by the hydrogenation using Pd/Ni catalyst in H-cube with gravity separation. Hydrolysis of in situ generated diazonium salts in the boiling acidic conditions is carried out using integration of flow and microwave-assisted synthesis. 58% of 4-isopropyl phenol was obtained. The sequential flow synthesis can be applied to synthesize other organic compounds involving this specific sequence of reactions.

NITROGEN-CONTAINING BIOPOLYMER-BASED CATALYSTS, THEIR PREPARATION AND USES IN HYDROGENATION PROCESSES, REDUCTIVE DEHALOGENATION AND OXIDATION

The present invention relates to a process for the preparation of a nitrogen containing biopolymer-based catalyst by pyrolysis of a metal complex with a nitrogen-containing biopolymer and to the nitrogen containing biopolymer-based catalysts obtainable by this process. In particular, the invention relates to a nitrogen containing biopolymer-based catalyst comprising metal particles and at least one nitrogen containing carbon layer. The invention also relates to the use of a nitrogen containing biopolymer-based catalyst in a hydrogenation process, preferably in a process for hydrogenation of nitroarenes, nitriles or imines; in a reductive dehalogenation process of C-X bonds, wherein X is CI, Br or I, preferably in a process for dehalogenation of organohalides or in a process for deuterium labelling of arenes via dehalogenation of organohalides; or in an oxidation process. Further, the invention relates to a metal complex with the nitrogen containing biopolymer, wherein the metal is a transition metal selected from the group consisting of manganese, ruthenium, cobalt, rhodium, nickel, palladium and platinum, preferably cobalt or nickel, and wherein the nitrogen containing biopolymer is selected from chitosan, chitin and a polyamino acid, preferably chitosan or chitin.

Selective Cross-Coupling of (Hetero)aryl Halides with Ammonia to Produce Primary Arylamines using Pd-NHC Complexes

Herein we report the first example of (hetero)arylation of ammonia using a monoligated palladium-NHC complex. The new, rationally designed, precatalyst (DiMeIHeptCl)Pd(allyl)Cl featuring highly branched alkyl chains has been shown to be effective in selective aminations across a range of challenging substrates, including nitrogen-containing heterocycles and those featuring base-sensitive functionality. The less bulky Pd-PEPPSI-IPentCl precatalyst performs well for ortho-substituted aryl halides, giving monoarylated products in high yield with good selectivity.

Biomass-Derived Catalysts for Selective Hydrogenation of Nitroarenes

Development of catalytically active materials from biowaste represents an important aspect of sustainable chemical research. Three heterogeneous materials were synthesized from inexpensive biomass-based chitosan and abundant Co(OAc)2 using complexation followed by pyrolysis at various temperatures. These materials were applied in the catalytic hydrogenation of nitroarenes using molecular hydrogen. A variety of diversely functionalized nitroarenes including some pharmaceutically active compounds were converted into aromatic amines in high yields, with high selectivity, and with excellent functional group tolerance. This green protocol has also been implemented for the synthesis of a biologically important TRPC3 inhibitor.

Co-based heterogeneous catalysts from well-defined Α-diimine complexes: Discussing the role of nitrogen

Ar-BIANs and related α-diimine Co complexes were wet impregnated onto Vulcan XC 72 R carbon black powder and used as precursors for the synthesis of heterogeneous supported nanoscale catalysts by pyrolysis under argon at 800?°C. The catalytic materials feature a core-shell structure composed of metallic Co and Co oxides decorated with nitrogen-doped graphitic layers (NGr). These catalysts display high activity in the liquid phase hydrogenation of aromatic nitro compounds (110?°C, 50 bar H2) to give chemoselectively substituted aryl amines. The catalytic activity is closely related to the amount and type of nitrogen atoms in the final catalytic material, which suggests a heterolytic activation of dihydrogen.

Electron-Transfer and Hydride-Transfer Pathways in the Stoltz–Grubbs Reducing System (KOtBu/Et3SiH)

Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert-butoxide react to form a highly attractive and versatile system that shows (reversible) silylation of arenes and heteroarenes as well as reductive cleavage of C?O bonds in aryl ethers and C?S bonds in aryl thioethers. Their extensive mechanistic studies indicate a complex network of reactions with a number of possible intermediates and mechanisms, but their reactions likely feature silyl radicals undergoing addition reactions and SH2 reactions. This paper focuses on the same system, but through computational and experimental studies, reports complementary facets of its chemistry based on a) single-electron transfer (SET), and b) hydride delivery reactions to arenes.

Reduction of nitroarenes using CO and H2O in the presence of a nanostructured cobalt oxide/Nitrogen-Doped Graphene (NGr) catalyst

The most common route to anilines is based on the reduction of the corresponding nitroarenes. In general, hydrogen is preferred as reducing agent and numerous catalytic systems are known to achieve such transformations. Besides, the use of CO/H2O as hydrogen source offers interesting possibilities for reductions. Carbon monoxide is a cheap and abundant chemical used on industrial scale for a variety of transformations. Although the reduction of nitroarenes with CO/H2O is known in the presence of noble-metal catalysts, earth-abundant inexpensive catalysts showing high selectivity have not yet been developed. In this respect, herein we present the use of a heterogeneous cobalt oxide catalyst (Co3O4/NGr@C), which is modified by nitrogen-doped graphene layers. Using this non-noble metal catalyst nitroarenes are reduced in high yields and good chemoselectivities.

USE OF THERMALLY-TREATED SUPPORTED COBALT CATALYSTS COMPRISING A POLYCYCLIC AROMATIC STRUCTURE CONSISTING OF NITROGEN LIGANDS FOR HYROGENATING AROMATIC NITRO COMPOUNDS

The invention relates to the use of thermally-treated supported cobalt catalysts for hydrogenating aromatic nitro compounds, the cobalt catalysts having been prepared by in situ immobilization of a cobalt-amine complex on an inorganic porous support and subsequent pyrolysis, and, in the cobalt-amine complex used, cobalt being present bonded to an aromatic or heterocyclic nitrogen ligand L, the nitrogen ligand being selected so as to form a polyaromatic structure with the cobalt atom.