123367-25-9

Usage

Uses

Used in Organic Synthesis:
DMAPP is utilized as a reagent in the synthesis of a variety of organic compounds, such as pharmaceuticals and agrochemicals, due to its chemical properties that facilitate the formation of desired products.
Used in Heterocyclic Compound Preparation:
In the field of organic chemistry, DMAPP is employed in the preparation of heterocyclic compounds, which are important for the development of new pharmaceuticals and other specialty chemicals.
Used as a Catalyst in Organic Reactions:
DMAPP also serves as a catalyst to enhance the efficiency and selectivity of various organic reactions, thereby improving the overall yield and purity of the target compounds.
Used in Medicinal Chemistry:
Given its potential biological activities, DMAPP is studied for its anti-inflammatory and antitumor properties, indicating its use in the development of new therapeutic agents for treating inflammation and cancer.
Used in Pharmaceutical Industry:
DMAPP is used as a key intermediate in the production of pharmaceuticals, contributing to the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
In agrochemicals, DMAPP is used in the synthesis of compounds that can help in the development of pesticides and other agricultural chemicals, aiming to increase crop yields and protect plants from pests and diseases.

Upstream product

• 1122-62-9 2-acetylpyridine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 127-19-5 N,N-dimethyl acetamide 
• 98-86-2 acetophenone 
• 25408-61-1 Ν,Ν-dimethylacetamide dimethyl acetal 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 75415-03-1 2-(1H-pyrazol-3-yl)pyridine 
• 138785-70-3 (+)-2-<1-(1-Phenylethyl)-5-pyrazolyl>pyridin 
• 52997-82-7 4-(pyridin-2-yl)pyrimidine 
• 1148-79-4 2,2':6,2''-terpyridine 
• 938066-21-8 2-(1-methyl-1H-5-pyrazolyl)pyridine 
• 162435-06-5 1-methyl-3-(pyridin-2-yl)-1H-pyrazole 
• 35299-71-9 2,6-bis(thiophen-2-yl)pyridine 
• 123760-40-7 6-(thiophen-2-yl)-2,2'-bipyridine 
• 320416-38-4 7-(2-pyridyl)-1,2,4-triazolo[1,5-a]pyrimidine 
• 66521-65-1 4-(pyridin-2-yl)pyrimidine-2-ylamine 
• 872672-74-7 N-(4-methyl-3-(4-(pyridin-2-yl)pyrimidin-2-ylamino)phenyl)-4-((4-methylpiperazin-1-yl)methyl) benzamide 
• 881677-39-0 4-chloromethyl-N-[4-methyl-3-(4-pyridin-2-yl-pyrimidin-2-ylamino)-phenyl]-benzamide 
• 475587-24-7 N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyridinamine 
• 475587-23-6 N-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine 

Relevant academic research and scientific papers

Addressing the poly- to oligo-ketone selectivity in styrene carbonylation catalyzed by palladium/bpy complexes. effect of the 6-alkyl substitution

Two series of organometallic Pd complexes, namely, (i) [Pd(CH 3)(CH3CN)(N-N′)][PF6] and (ii) [Pd(CH3)(N-N′)2][PF6], with a range of 6-alkyl-substituted-2,2′-bipyridine ligands, including the new 6-(1-methoxyethyl)-2,2′-bipyridine, in both racemic and enantiopure form, and 2-(methoxymethyl)-6-(1H-1,2,3-triazol-1-yl)pyridine, have been studied. 6-(1-Methoxyethyl)-2,2′-bipyridine was synthesized both in racemic and in the opposite homochiral enantiomeric forms by two stereocomplementary chemoenzymatic procedures. The characterization of the new complexes, both in solid state and in solution, provides evidence for the formation of a unique isomer featuring the methyl ligand trans to the Pd-N bond of the substituted pyridine ring. For the complex with the bpy ligand having the sec-butyl substituent a cyclometalation reaction with the release of methane occurs, leading the substituted bpy to act as a terdentate N-N′-C ligand. Complexes of series ii feature one chelate N-N′ ligand, while the other one is coordinated to Pd in a monodentate fashion. In solution a fluxional process that makes equivalent the two N-N′ ligands is present, and the static 1H NMR spectra correspond to an averaged structure where palladium is a stereogenic center. All these complexes behave as catalysts for styrene carbonylation, yielding CO/styrene oligoketones, which are optically active when catalysts containing chiral, enantiomerically pure, ligands are applied. For both series of complexes the reactivity with labeled CO has been investigated, leading to the formation of the corresponding Pd-acetyl species, with that for complexes of series ii featuring both N-N′ molecules bonded to the same metal center.

A family of polyoxometalate-resorcin[4]arene-based metal–organic materials: Assemblies, structures and lithium ion battery properties

Polyoxometalates (POMs) are alternative anode materials of lithium ion batteries (LIBs) for their reversible electrochemical redox behaviors and electron storage functions. To overcome the low conductivity and poor stability of the POMs, embedment of POMs into metal–organic hybrid complexes is a promising synthetic strategy. Here, we designed a family of copper-containing POM-resorcin[4]arene-based complexes supported by a resorcin[4]arene ligand (TPTR4A), copper cations and Keggin-type POMs, namely, [Cu4(TPTR4A)2][PMo12O40](OH)·2DMA·H2O (1a), [Cu4(TPTR4A)2][SiW12O40]·2.5DMA (1b) and [Cu4(TPTR4A)2][PW12O40](OH)·0.5DMA·5H2O (1c) (DMA = N,N’-dimethylacetamide). To improve the conductivity of the complexes, composites 1a@GO-1c@GO were obtained through mechanical grinding of the complexes and graphene oxide (GO). Strikingly, they show high initial specific capacity and stability for LIBs. This work offered a strategy for application of the POM-based complexes as LIBs via combining POM-based complexes and RGO.

A convenient set of bidentate pyridine ligands for combinatorial synthesis

Synthesis is reported of five pyridine-containing bidentate ligands bearing nucleophilic groups at different positions. Their efficient solid- phase alkylation was demonstrated in the synthesis of a small library. These ligands are attractive building blocks for the construction of libraries of metal-binding compounds for various purposes.

Structure-dependent regioselectivity of a roll-over cyclopalladation occuring at 2,2′-bipyridine-type ligands

In this work, different bipyridine-analogue ligands bearing a dimethylamino group in the meta-position of one of the heterocyclic rings were synthesized and reacted with palladium(II) acetate under identical conditions. Cyclometallated palladium(II) complexes with C,N- or C,N,N’-coordinating chelate ligands are formed which were characterized by elemental analysis, 1H and 13C NMR spectroscopy, and single crystal X-ray diffraction analysis. In the case of the mononuclear, C,N,N’-coordinated complex, which is formed by an attack of the palladium(II) site at of the N-methyl groups, the primarily coordinating acetato ligand is exchanged against a chlorido ligand, which is liberated from the solvent dichloromethane by a nucleophilic substitution reaction. In contrast, cyclometallation occurring at one of the six-membered heterocycles leads to dinuclear acetato-bridged palladium(II) complexes.

Synthesis, characterisation and application of iridium(III) photosensitisers for catalytic water reduction

The synthesis of novel, monocationic iridium(III) photosensitisers (Ir-PSs) with the general formula [IrIII(C^N)2(N^N)]+ (C^N: cyclometallating phenylpyridine ligand, N^N: neutral bidentate ligand) is described. The structures obtained were examined by cyclic voltammetry, UV/Vis and photoluminescence spectroscopy and X-ray analysis. All iridium complexes were tested for their ability as photosensitisers to promote homogeneously catalysed hydrogen generation from water. In the presence of [HNEt 3][HFe3(CO)11] as a water-reduction catalyst (WRC) and triethylamine as a sacrificial reductant (SR), seven of the new iridium complexes showed activity. [Ir(6-iPr-bpy)(ppy)2]PF 6 (bpy: 2,2′-bipyridine, ppy: 2-phenylpyridine) turned out to be the most efficient photosensitiser. This complex was also tested in combination with other WRCs based on rhodium, platinum, cobalt and manganese. In all cases, significant hydrogen evolution took place. Maximum turnover numbers of 4550 for this Ir-PS and 2770 for the Fe WRC generated in situ from [HNEt 3][HFe3(CO)11] and tris[3,5- bis(trifluoromethyl)phenyl]phosphine was obtained. These are the highest overall efficiencies for any Ir/Fe water-reduction system reported to date. The incident photon to hydrogen yield reaches 16.4 % with the best system. Copyright

Mechanistic Studies on Ruthenium(II)-Catalyzed Base-Free Transfer Hydrogenation Triggered by Roll-Over Cyclometalation

The synthesis of 2-substituted pyridine–pyrimidine ligands and their complexation with arene ruthenium(II) chloride moieties is reported. Depending on the electronic and steric influences of the ligand, the catalysts undergo CH activation by roll-over cyclometalation. This process opens up the route to the catalytic transfer hydrogenation of ketones with isopropanol as the hydrogen source under base-free and mild conditions. Barriers related to the roll-over cyclometalation process can be determined experimentally by collision-induced dissociation ESI mass spectrometry. They are supported by DFT calculations and allow the classification of the ligands according to their electronic and steric properties, which is also in accordance with critical bond parameters derived from X-ray structure data. DFT calculations furthermore reveal that the formation of a ruthenium(II) hydrido species is plausible through β-hydride elimination from isopropanol.

Study of the coordination and solution structures for the interaction systems between diperoxidovanadate complexes and 4-(pyridin-2-yl)pyrimidine-like ligands

To understand the substitution effects of 4-(pyridin-2-yl)pyrimidine (pprd) on the coordination reaction equilibria, the interactions between a series of the pprd-like ligands and [OV(O2)2(H2O)] - or [OV(O2)2(HOD)]- or [OV(O 2)2(D2O)]- (bpV) have been explored by a combination of multinuclear (1H, 13C, and 51V) magnetic resonance, heteronuclear single quantum coherence (HSQC) and variable temperature NMR in a 0.15 mol L-1 NaCl D 2O solution that mimics physiological conditions. The direct NMR data are reported for the first time. Competitive coordination interactions result in a series of new hepta-coordinated peroxidovanadate species [OV(O 2)2LL′]- (LL′ = pprd-like chelating ligands). The equilibrium constants for the products between bpV and the pprd-like ligands show that the relative affinity of the ligands is pprd ≈ 2-NH2-pprd > 2-Me-pprd > 2-Et-pprd > 4-(6-methylpyridin-2- yl)pyrimidine (abbr. 6′-Me-pprd). When the ligand is pprd, a pair of isomers (Isomer A and B) are observed in aqueous solution, which are attributed to the different types of coordination modes between the metal and the ligands, while the crystal structure of NH4[OV(O2) 2(pprd)]·2H2O has the same coordination structure as Isomer A. For substituted pprd ligands, however, only one type of structure (Isomer A or B) is observed in solution. These results demonstrate that, when the aromatic ring has a substitution group, both the steric effect (from the alkyl) and hydrogen bonding (from the amine) can affect the coordination reaction equilibrium to prevent the appearance of either Isomer B in solution for the ligands 2-Me-pprd, 2-NH2-pprd, 2-Et-pprd, or Isomer A in solution for 6′-Me-pprd. The Royal Society of Chemistry 2012.

Molecular squares, rectangles and infinite helical chains utilising the simple 'corner' ligand 4-(2-pyridyl)-pyrimidine

The ligand 4-(2-pyridyl)-pyrimidine forms multinuclear Ag(I) complexes by a combination of chelating and bridging coordination modes; molecular shape (square or rectangle) and degree of aggregation depend on the anion used.

Selective Extraction of Americium(III) over Europium(III) with the Pyridylpyrazole Based Tetradentate Ligands: Experimental and Theoretical Study

1,3-Bis[3-(2-pyridyl)pyrazol-1-yl]propane (Bippp) and 1,2-bis[3-(2-pyridyl)pyrazyl-1-methyl]benzene (Dbnpp), the pyridylpyrazole based tetradentate ligands, were synthesized and characterized by MS, NMR, and FT-IR. The solvent extraction and complexation

Excited-State Kinetics of an Air-Stable Cyclometalated Iron(II) Complex

The complex class [Fe(N^N^C)(N^N^N)]+ with an Earth-abundant metal ion has been repeatedly suggested as a chromophore and potential photosensitizer on the basis of quantum chemical calculations. Synthesis and photophysical properties of the parent complex [Fe(pbpy)(tpy)]+ (Hpbpy=6-phenyl-2,2′-bipyridine and tpy=2,2′:6′,2′′-terpyridine) of this new chromophore class are now reported. Ground-state characterization by X-ray diffraction, electrochemistry, spectroelectrochemistry, UV/Vis, and X-ray spectroscopy in combination with DFT calculations proves the high impact of the cyclometalating ligand on the electronic structure. The photophysical properties are significantly improved compared to the prototypical [Fe(tpy)2]2+ complex. In particular, the metal-to-ligand absorption extends into the near-IR and the 3MLCT lifetime increases by 5.5, whereas the metal-centered excited triplet state is very short-lived.