2,2'-Bipyridine | Pyridines

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Quality Control of 2,2'-Bipyridine Purity: 97% SDS Specification

COA

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NMR

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HPLC

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Product Citations Show More

Reduction of CO to Methanol with Recyclable Organic Hydrides

Andressa V. Müller ; Shahbaz Ahmad ; Jake T. Sirlin ; Mehmed Z. Ertem ; Dmitry E. Polyansky ; David C. Grills , et al.

DOI: 10.1021/jacs.3c14605 JACS,2024,146(15):10524-10536.

Abstract: The reaction steps for the selective conversion of a transition metal carbonyl complex to a hydroxymethyl complex that releases methanol upon irradiation with visible light have been successfully quantified in acetonitrile solution with dihydrobenzimidazole organic hydride reductants. Dihydrobenzimidazole reductants have been shown to be inactive toward H2 generation in the presence of a wide range of proton sources and have been regenerated electrochemically or photochemically. Specifically, the reaction of cis-[Ru(bpy)2(CO)2]2+ (bpy = 2,2′-bipyridine) with one equivalent of a dihydrobenzimidazole quantitatively yields a formyl complex, cis-[Ru(bpy)2(CO)(CHO)]+, and the corresponding benzimidazolium on a seconds time scale. Kinetic experiments revealed a first-order dependence on the benzimidazole hydride concentration and an unusually large kinetic isotope effect, inconsistent with direct hydride transfer and more likely to occur by an electron transfer-proton-coupled electron transfer (EΤ−PCET) or related mechanism. Further reduction/protonation of cis-[Ru(bpy)2(CO)(CHO)]+ with two equivalents of the organic hydride yields the hydroxymethyl complex cis-[Ru(bpy)2(CO)(CH2OH)]+. Visible light excitation of cis-[Ru(bpy)2(CO)(CH2OH)]+ in the presence of excess organic hydride was shown to yield free methanol. Identification and quantification of methanol as the sole CO reduction product was confirmed by 1H NMR spectroscopy and gas chromatography. The high selectivity and mild reaction conditions suggest a viable approach for methanol production from CO, and from CO2 through cascade catalysis, with renewable organic hydrides that bear similarities to Nature’s NADPH/NADP+.

Purchased from AmBeed: 3171-45-7 ; 25148-68-9 ; 366-18-7

Carbon-centered radical capture at nickel(II) complexes: Spectroscopic evidence, rates, and selectivity

Qiao Lin ; Ethan H. Spielvogel ; Tianning Diao ;

DOI: 10.1016/j.chempr.2023.02.010 Chem,2023,9(5):1295-1308.

Abstract: The capture of carbon-centered radicals at a nickel(II) center is commonly featured in recent cross-coupling and metallaphotoredox catalytic reactions. Despite its widespread application in catalysis, this fundamental step lacks experimental characterization. This report portrays radical capture at catalytically relevant nickel(II) centers from several aspects, including the structure-activity relationships of the ligands, the mechanism, the kinetics, and the stereoselectivity. Spectroscopic data provide evidence for the formation of a nickel(III) intermediate. Strikingly different reactivity between nickel-aryl and nickel-alkyl complexes implies different rate-determining steps for C(sp3)–C(sp3) and C(sp2)–C(sp3) bond formation. Kinetic data benchmark the capture rates on the scale of 10[7] M−1s−1 and 10[6] M−1s−1 for primary and secondary radicals, respectively. Overall, the activation energy is higher than that of previous computational estimations. Finally, stoichiometric experiments with well-defined chiral nickel complexes demonstrate that the radical trapping step can confer diastereoselectivity and enantioselectivity with a drastic ligand effect.

Purchased from AmBeed: 142946-79-0 ; 50487-71-3 ; 3395-91-3 ; 22980-76-3 ; 2706576-80-7 ; 119165-69-4 ; 402-43-7 ; 27060-75-9 ; 6346-09-4 ; 117408-98-7 ; 957034-45-6 ; 7318-00-5 ; 403-39-4 ; 366-18-7 ; 401-79-6 ; 929000-62-4 ; 459-47-2 ; 1416819-91-4 ; 605-39-0 ; 44565-27-7 ; 10285-80-0 ; 458-76-4 ; 5789-35-5 ; 1165-06-6 ; 1595706-68-5 ; 27820-98-0

Versatile Nanoporous Organic Polymer Catalyst for the Size- Selective Suzuki-Miyaura Coupling Reaction

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon ; Swager, Timothy M. ;

DOI: 10.1021/acsanm.2c04393 ACS Appl. Nano Mater.,2022,5(12):18603-18611.

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Purchased from AmBeed: 128796-39-4 ; 10365-98-7 ; 98-80-6 ; 556-96-7 ; 171663-13-1 ; 71597-85-8 ; 402-43-7 ; 2042-37-7 ; 22385-77-9 ; 16419-60-6 ; 15862-18-7 ; 87199-15-3 ; 171408-84-7 ; 643-58-3 ; 591-50-4 ; 76911-73-4 ; 398-36-7 ; 14871-92-2 ; 5720-07-0 ; 945976-76-1 ; 366-18-7 ; 2920-38-9 ; 623-00-7 ; 24973-49-7 ; 588-59-0 ; 128796-39-4 ; 5723-93-3 ; 17057-88-4 ; 126485-55-0

Product Details of 2,2'-Bipyridine

CAS No. :	366-18-7
Formula :	C₁₀H₈N₂
M.W :	156.18
SMILES Code :	C1(C2=NC=CC=C2)=NC=CC=C1
MDL No. :	MFCD00006212
InChI Key :	ROFVEXUMMXZLPA-UHFFFAOYSA-N
Pubchem ID :	1474

Safety of 2,2'-Bipyridine

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301+H311
Precautionary Statements:	P264-P270-P280-P301+P310-P302+P352+P312-P361+P364
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of 2,2'-Bipyridine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 366-18-7 ]
Downstream synthetic route of [ 366-18-7 ]

[ 366-18-7 ] Synthesis Path-Upstream 1~1

1
[ 366-18-7 ]
[ 178039-84-4 ]

References: [1] Journal of the Chemical Society, 1938, p. 1662,1669.
[2] Organic Letters, 2015, vol. 17, # 6, p. 1497 - 1500.
[3] Organometallics, 2016, vol. 35, # 15, p. 2429 - 2432.

[ 366-18-7 ] Synthesis Path-Downstream 1~35

1
[ 366-18-7 ]
[ 17217-57-1 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 315 - 319.
[2]Advanced Synthesis and Catalysis,2003,vol. 345,p. 497 - 505.

2
[ 366-18-7 ]
[ 52522-40-4 ]
[ 81191-64-2 ]

References: [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1981,vol. 11,p. 517 - 524.

3
[ 366-18-7 ]
[ 940-07-8 ]
copper(II) acetate dihydrate [ No CAS ]
[ 7732-18-5 ]
[Cu(pyrazine-2,6-dicarboxylic acid-2H)(2,2'-bipyridine)(H₂O)]*2.5H₂O [ No CAS ]

References: [1]Inorganica Chimica Acta,2007,vol. 360,p. 2029 - 2038.

4
[ 366-18-7 ]
[ 940-07-8 ]
[ 5970-45-6 ]
[Zn(pyrazine-2,6-dicarboxylate)(2,2'-bipiridine)H₂O]*0.5H₂O [ No CAS ]

References: [1]Journal of Molecular Structure,2007,vol. 832,p. 48 - 54.

5
[ 366-18-7 ]
[ 940-07-8 ]
[ 7732-18-5 ]
[ 6147-53-1 ]
[Co(pyrazine-2,6-dicarboxylic acid(-2H))(2,2'-bipyridine)(H₂O)]*0.5H₂O [ No CAS ]

References: [1]Polyhedron,2008,vol. 27,p. 717 - 726.

6
[ 366-18-7 ]
[ 5970-45-6 ]
[ 130-85-8 ]
[ 1095905-74-0 ]

References: [1]Journal of Molecular Structure,2008,vol. 891,p. 364 - 369.

7
[ 366-18-7 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 130-85-8 ]
[Cd(pamoic acid)(2,2'-bipyridine)2]n [ No CAS ]

References: [1]Journal of Molecular Structure,2008,vol. 891,p. 364 - 369.

8
[ 366-18-7 ]
copper(II) perchlorate hexahydrate [ No CAS ]
[ 557-24-4 ]
catena-poly[(2,2'-bipyridine-κ2N,N')(μ3-maleato-κ3O,O',O'')-copper(II)] dihydrate [ No CAS ]