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Application In Synthesis of 1,2-Bis(diphenylphosphino)ethane. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1,2-Bis(diphenylphosphino)ethane, is researched, Molecular C26H24P2, CAS is 1663-45-2, about Tertiary phosphine-appended transition metal ferrocenyl dithiocarbamates: Syntheses, Hirshfeld surface, and electrochemical analyses. Author is Singh, Amita; Dutta, Archisman; Singh, Ashish Kumar; Trivedi, Manoj; Kociok-Koehn, Gabriele; Muddassir, Mohd.; Kumar, Abhinav.

Five new heteroleptic complexes of Cu(I), Ag(I), and Ni(II) having formulas [Cu3(dtc)2(dppf)2]PF6 (Cu-I), [Cu3(dtc)2(dppe)2]PF6 (Cu-II), [Cu(PPh3)2(dtc)] (Cu-III), [Ag3(dtc)2(PPh3)2]NO3 (Ag-I), and [Ni(dtc)(dppf)]PF6 (Ni-I) (dtc = N-ethanol-N-methylferrocenyl-dithiocarbamate; dppf = 1,1′-bis(diphenylphosphino)ferrocene; dppe = 1,1′-bis(diphenylphosphino)ethane; PPh3 = tripheylphosphine) have been synthesized and characterized using elemental anal., Fourier-transform IR, multinuclear NMR, UV-Vis spectroscopy, and single-crystal X-ray diffraction. The single-crystal X-ray diffraction studies indicate that Ag-I forms a rare trinuclear cluster in which the geometry around the two silver centers Ag1 and Ag3 is distorted tetrahedral, whereas the third silver center Ag2 shows a distorted trigonal planar geometry. The Ni-I complex has a distorted square-planar geometry around the Ni center. In addition, a side product [Ag2{S2(dppf)2}] (Ag-II) was obtained during an attempt to synthesize [Ag(dppf)(dtc)], where the two Ag centers are bridged by two sulfido centers and coordinated with two phosphorus centers of the dppf ligand to give rise to a distorted tetrahedral geometry. The solid-state structures of Ag-I, Ni-I, and Ag-II are stabilized by a variety of weak interactions. The nature of these interactions has been addressed with the help of Hirshfeld surface analyses. In addition, the weak argentophilic interaction in Ag-I and Ag-II have been studied using quantum theory of atoms in mols. and natural bond orbital calculations The electrochem. properties of the complexes have been investigated using cyclic voltammetry, where Cu-I and Cu-II exhibited two quasi-reversible waves, whereas Cu-III, Ag-I, Ag-II, and Ni-I exhibited only one quasi-reversible peak.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about A rapid and novel method for the synthesis of 5-substituted 1H-tetrazole catalyzed by exceptional reusable monodisperse Pt NPs@AC under the microwave irradiation.Application of 14389-12-9.

A series of 5-substituted 1H-tetrazoles I (R = 4-O2NC6H4, 4-BrC6H4, 4-MeC6H4, etc.) were synthesized in DMF by the [3 + 2] cycloaddition reaction under the effect of microwave irradiation (10-30 min, fixed mode, 90 °C, 140 W) in the presence of highly efficient superior catalyst. For this reaction, different aromatic nitriles with the sodium azide were used and superior monodisperse (Md) platinum nanoparticles (Pt NPs) decorated on activated carbon (AC) served as a catalyst. Md-Pt NPs@AC were reproducibly and easily produced by double solvent reduction of PtCl4 in room temperature and characterized by transmission electron microscopy (TEM), the high resolution electron micrograph (HRTEM), X-ray diffraction (XRD), at. force microscopy (AFM) and XPS. The sum of their results shows the formation of highly crystalline and colloidally stable Md-Pt NPs@AC. The catalytic performance of these new NPs were investigated for the synthesis of 5-substituted 1H-tetrazoles, in which they were found to be exceptional reusable, isolable, stable and highly efficient heterogeneous catalyst. All prepared tetrazole products were obtained with perfect yield by using current heterogeneous catalyst.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Synthetic Route of C6H5N5. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about Synthesis of 5-substituted 1H-tetrazoles from aryl halides using nanopolymer-anchored palladium(II) complex as a new heterogeneous and reusable catalyst. Author is Tajbakhsh, Mahmood; Alinezhad, Heshmatollah; Nasrollahzadeh, Mahmoud; Kamali, Taghi A..

This paper reports on the preparation and use of chloromethylated polystyrene-anchored palladium(II) complex, [Ps-ttet-Pd(II)], as a separable nanocatalyst for the synthesis of 5-substituted 1H-tetrazoles by treating aryl halides with K4[Fe(CN)6] as non-toxic cyanide source, to generate in situ the corresponding aryl nitriles which then react through [2 + 3] cycloaddition with sodium azide. High yields of the products, simple methodol., easy work-up procedure, high catalytic activity and superior cycling stability of the catalyst are the main advantages of this protocol. The structure of the catalyst was characterized using the powder XRD, SEM, TG-DTA, EDS, AAS, and FT-IR spectroscopy techniques.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 14389-12-9, is researched, Molecular C6H5N5, about γ-Fe2O3. A magnetic separable catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide, the main research direction is nitrile cycloaddition sodium azide iron oxide catalyst; tetrazole preparation.Safety of 5-(4-Pyridyl)-1H-tetrazole.

An efficient route for the synthesis of 5-substituted 1H-tetrazole via [2+3] cycloaddition of nitriles and sodium azide is reported using γ-Fe2O3 nanoparticles as a magnetic separable catalyst. Under optimized conditions, the moderate to good yields (71-95%) were obtained. The catalyst was easily separated by a magnet and reused for several circles.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 3411-48-1, is researched, SMILESS is C1=CC2=C(C=C1)C(=CC=C2)P(C1=CC=CC2=C1C=CC=C2)C1=CC=CC2=C1C=CC=C2, Molecular C30H21PJournal, Marine Chemistry called Characterization of minerals and organic phosphorus species in marine sediments using soft x-ray fluorescence spectromicroscopy, Author is Brandes, Jay A.; Ingall, Ellery; Paterson, David, the main research direction is mineral organic phosphorus species marine sediment; soft Xray fluorescence spectromicroscopy.Synthetic Route of C30H21P.

Phosphorus Near Edge X-ray Fluorescence Spectroscopy (P-NEXFS) data were collected on phosphorus containing phases including organic and inorganic compounds and minerals. Although phases containing P in the plus five oxidation state P(V) in a tetrahedral PO4 structure have similar primary fluorescence peak positions, the size, shape, and positions of secondary spectral features are diagnostic for different compounds and minerals. In particular, Ca phosphates exhibited a notable post-peak shoulder at 2154.5 eV, while oxidized iron phosphates had a distinctive pre-peak feature at 2148 eV. Polyphosphates have a broad secondary peak located ∼2 eV higher in energy than a similar feature in phosphate esters and diesters. Compounds containing P(V) in structures other than PO4 tetrahedra such as phosphonates have a primary peak shifted ∼1 eV lower than corresponding organo-phosphates. Organo-phosphates with P in the plus 3 oxidation state P(III) such as phosphines had primary fluorescence peaks shifted still further down in energy (2-3 eV). The substitution of aromatic C groups in close proximity to P structures in organic compounds generated both pre- and post-peak features as well as a number of secondary peaks. X-ray fluorescence mapping of P, Si, Al, Mg, and Na was conducted on a marine sediment sample with sub-micron spatial resolution Phosphorus was heterogeneously distributed in the sample and not correlated on a broad scale with any other element examined Much of the P present in the sample was located in small, 0.6-8 μm size, P-rich domains. Several P-rich regions were examined with P-NEXFS using a focused beam with 60 nm resolution and were found to consist of either calcium phosphate or polyphosphate phases. The presence of significant polyphosphate-dominated regions in a marine sediment sample supports the recent observations that such phases can play an important role in marine P cycling. The combination of fluorescence mapping and P-NEXFS data collection on fine particles provides a powerful new tool for environmental phosphorus studies.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Computed Properties of C30H21P. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Tri(naphthalen-1-yl)phosphine, is researched, Molecular C30H21P, CAS is 3411-48-1, about Selective hydroformylation of 1-hexene to branched aldehydes using rhodium complex of modified bulky phosphine and phosphite ligands.

The selective hydroformylation of 1-hexene to branched aldehydes was investigated using rhodium complex of tri-1-naphthylphosphine PNp3 and tri-1-naphthylphosphite P(ONp)3. The PNp3 and P(ONp)3 ligands having more steric nature than PPh3 enhanced the formation of branched aldehydes at 110 °C and 4.0 MPa syngas pressure. The branched aldehyde selectivity increased remarkably (82%) by adding P(ONp)3 as auxiliary ligand in Rh/PNp3 catalyzed hydroformylation of 1-hexene. The high selectivity for the branched aldehydes is due to rapid alkene isomerization producing internal alkenes followed by hydroformylation to yield branched aldehydes.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 14389-12-9, is researched, Molecular C6H5N5, about Unprecedented Application of Flexible Bis(pyridyl-tetrazole) Ligands To Construct Helix/Loop Subunits To Modify Polyoxometalate Anions, the main research direction is silver pyridyltetrazole molybdophosphate tungstophosphate polyoxometalate preparation structure electrochem catalyst; electrocatalyst photocatalyst silver pyridyltetrazole molybdophosphate tungstophosphate; crystal structure silver pyridyltetrazole molybdophosphate tungstophosphate dimer coordination polymer.Application of 14389-12-9.

By introducing the unprecedented and flexible isomeric bis(pyridyl-tetrazole) ligands into a polyoxometalates (POMs) system, three POM-based compounds, {Ag2(4-bptzb)2(H2O)2[H2PMo12O40]2}·4-bptzb·5H2O (1), [Ag4(3-bptzb)2(PMoVMoVI11O40)]·2H2O (2), and Ag3(3-bptzb)2.5(H2O)2[H3P2W18O62] (3) [4-bptzb = 1,4-bis(5-(4-pyridyl)tetrazol-2-yl)butane and 3-bptzb = 1,4-bis(5-(3-pyridyl)tetrazol-2-yl)butane], were synthesized under hydrothermal conditions and structurally characterized by single-crystal x-ray diffraction analyses. Compound 1 exhibits a dimeric structure constructed from two Keggin [PMo12O40]3- anions and a binuclear [Ag2(trans-4-bptzb)2]2+ subunit in which the trans-4-bptzb acts as a bidentate bridging ligand with one tetrazolyl group. In 2, the 3-bptzb acts as a tetradentate bridging ligand with the tetrazolyl and pyridyl groups linking AgI ions to generate a 3D metal-organic framework (MOF), which contains charming meso-helix chains. The Keggin anions acting as bidentate inorganic ligands reside in the distorted tetragonal channels of the MOF. In compound 3, the 3-bptzb adopts versatile coordination modes linking AgI ions to first construct loop connecting loop 1D chains, which are linked by {Ag[P2W18O62]}n zigzag chains to form a scarce hamburger-style 2D sheet. These adjacent sheets are further fused by 3-bptzb ligands to construct a 3D framework. The influences of isomeric bptzb ligands and POMs on the construction of Ag-bptzb subunits and the whole structures of the title compounds are discussed. The electrochem. behaviors and electrocatalytic activities of compounds 2 and 3 and their corresponding parent POMs as well as the fluorescent properties of the title compounds were studied. The photocatalytic activities of compounds 2 and 3 and their corresponding parent POMs for decomposition of methylene blue, rhodamine B, and Methyl orange under UV irradiation also were investigated.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensations of isatinic acid with ureas, ethyl carbamate, and guanidine》. Authors are Stefanovic, Gj.; Lorenc, L. J.; Mihailovic, M. Lj..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Recommanded Product: 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.

The title condensations gave high yields of 2-derivatives of quinazoline-4-carboxylic acid o-C6H4.N:CR’.N:CCO2R. KOH solution (20% aqueous) containing 0.1 mole KOH added to 14.7 g. isatin (II), the mixture warmed at 40° until yellow, the solution evaporated to dryness in vacuo below 40°, and the residue crystallized from EtOH gave K isatinate (III). Heating 4.06 g. III with 6.0 g. urea at 130-40° 10 hrs., treating the mixture with hot EtOH, and cooling gave 3.84 g. I(R = K, R’ = OH) (IV), which with aqueous AgNO3 was converted to I (R = Ag, R’ = OH) (V). V (2.97 g.) refluxed 6 hrs. with 2.13 g. MeI in 20 ml. anhydrous Et2O, the mixture filtered, the AgI washed with hot EtOH, the filtrate and washings combined, and evaporated to dryness in vacuo gave 2.18 g. crude I (R = Me, R’ = OH) (VI), m. 200-1° (EtOH). When anhydrous MeOH was used for washing and crystallization, VI crystallized with 1 mol. MeOH, m. 216°. IV (9.1 g.) in 90 ml. H2O treated at 5° with an equivalent amount of 8% aqueous HCl, the precipitate filtered off, and washed with cold H2O gave 7.5 g. I (R = H, R’ = OH) (VII).H2O, m. 264-5°, pK 3.10 (H2O-EtOH), which gave the anhydrous acid (VIII) on prolonged drying over P2O5 in vacuo. This (2.08 g.) treated dropwise with excess CH2N2 in anhydrous Et2O at ice-bath temperature gave, after evaporation of solvent, crude I (R = Me, R’ = OMe) (IX), m. 99-100° (EtOH). IX (240 mg.) refluxed 30 min. with 12 ml. 0.1N aqueous NaOH, the solution cooled to 5°, acidified with 5% aqueous HCl to Congo red, and filtered gave 190 mg. I (R = H, R’ = OMe) (X), m. 156° (purification through the Na salt). X (102 mg.) heated at 160° to cessation of CO2 evolution and the product sublimed at 10-15 mm. gave 48.2 mg. 2-methoxyquinazoline, m. 56°. Boiling 7.50 g. VIII in 75 ml. H2O 6 hrs., cooling, and filtering gave 5.0 g. crude 2-quinazolone (XI), converted to the hydrochloride, m. above 300°, by boiling concentrated HCl and addition of EtOH. This gave pure XI, m. 282-4°, with boiling EtOH. III (10.15 g.) heated with (H2N)2C:NH 4 hrs. at 125°, followed by dissolution with H2O, filtration, and acidification of the filtrate with 5% aqueous HCl to Congo red gave 8.9 g. I (R = H, R’ = NH2) (XII), which, after solution in NaHCO3 and precipitation with 5% sq. HCl, gave pure XII, m. 210°. Treating XII at 5° in Et2O with a slight excess of ethereal CH2N2, evaporating the solvent, and crystallizing the crude product from EtOH gave I (R = Me, R’ = NH2) (XIII), m. 144-5°. XII (100 mg.) decarboxylated at 220-5°/10-15 mm. yielded 63 mg. 2-aminoquinazolone, m. 205°, which sublimed during the decarboxylation. IV was also obtained in high yield by reaction of PhNHCONH2, Me2NCONH2, or NH2CO2Et with III. A discussion of lactim-lactam tautomerization was given, based on the methylation reactions and infrared spectra.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Reference of 1,2-Bis(diphenylphosphino)ethane. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 1,2-Bis(diphenylphosphino)ethane, is researched, Molecular C26H24P2, CAS is 1663-45-2, about Ranking Ligands by Their Ability to Ease (C6F5)2Ni(II)L → Ni0L + (C6F5)2 Coupling versus Hydrolysis: Outstanding Activity of PEWO Ligands. Author is Ponce-de-Leon, Jaime; Gioria, Estefania; Martinez-Ilarduya, Jesus M.; Espinet, Pablo.

The NiII literature complex cis-[Ni(C6F5)2(THF)2] is a synthon of cis-Ni(C6F5)2 that allows the authors to establish a protocol to measure and compare the ligand effect on the Ni(II) → Ni(0) reductive elimination step (coupling), often critical in catalytic processes. Several ligands of different types were submitted to this Ni-meter comparison: bipyridines, chelating diphosphines, monodentate phosphines, PR2(biaryl) phosphines, and PEWO ligands (phosphines with one potentially chelate electron-withdrawing olefin). Extremely different C6F5-C6F5 coupling rates, ranging from totally inactive (producing stable complexes at room temperature) to those inducing almost instantaneous coupling at 25°, were found for the different ligands tested. The PR2(biaryl) ligands, very efficient for coupling in Pd, are slow and inefficient in Ni, and the reason for this difference was examined In contrast, PEWO type ligands are amazingly efficient and provide the lowest coupling barriers ever observed for NiII complexes; they yield up to 96% C6F5-C6F5 coupling in 5 min at 25° (the rest is C6F5H) and 100% coupling with no hydrolysis in 8 h at -22 to -53°. The ability of ligands to facilitate a difficult C-C coupling and protect from hydrolysis in Ni(II) is very different from their performance in Pd(II). Most remarkably, PR2(biaryl) ligands with very good performance in Pd(II) are not efficient in Ni(II), whereas PEWO ligands are amazingly efficient and induce C6F5-C6F5 coupling even at -50°.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Related Products of 20198-19-0. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about Reactions of some quinazoline compounds with ethoxymethylenemalonic acid derivatives. Author is Deady, Leslie W.; Mackay, Maureen F.; Werden, Dianne M..

The reactions of Et (1,4-dihydro-4-oxoquinazolin-2-yl)acetate (I, R = CH2CO2Et) and 2-aminoquinazolin-4(1H)-one (I, R = NH2) with ethoxymethylenemalonate derivatives EtOHC:CR1R2 [R1 = R2 = CO2Et (II); R1 = CN, R2 = CN, CO2Et (III)] are reported, and different results are obtained to those previously found with quinoline analogs. Reaction of I (R = CH2CO2Et) with II gives a pyrido[1,2-a]quinazoline, while with III, 2-(pyridin-2-yl)aminobenzoates IV (R2 = CN, R3 = Et, CH2CH2CH; R2 = CO2Et, R3 = Et) are formed, presumably by ring-opening of intermediate pyrido[2,1-b]quinazolines. Reaction of I (R = NH2) with II likewise results in ultimate cyclization onto N-1 of the quinazoline, while reactions with III give isolable pyrimido[2,1-b]quinazolines. These are readily cleaved under mild conditions. The structure of IV (R2 = CN, R3 = Et) was proved by x-ray crystallog.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis