There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size

Price

VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock

{[ item.pr_size ]}

Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

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

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Citations Show More

Engineering Porosity in Porous Organic Polymers

Porath, Anthony J ;

Abstract: Porous aromatic frameworks (PAFs) are a class of rigid, exceptionally stable polymers that exhibit some of the highest surface areas observed for a fully organic material. The exhibit a high-degree of reaction dependent surface area measurements, with the same reaction, the Yamamoto-type Ullmann coupling, being used to synthesize all the highest surface area examples. We investigated the reaction features responsible for differences observed in polymers with the same formal structure synthesized through different reaction routes. Our hypothesis being that differences were due to defects, or departures from the anticipated structure, in the lower surface area examples. These defects would decrease the overall rigidity of the PAF, allowing it to collapse to a denser, less porous phase. Chapter 2 reports the first measurement of native defectivity in PAFs and explores how increasingly defective structures in PAFs lead to lower surface area materials. Notably, we now understand the relationship between coupling efficiency and surface area, imparting us with an important design principle for the creation of new reaction routes towards high surface area PAFs. With the importance of coupling efficiency now known, we then explored opportunities to modify the Yamamoto-type Ullmann coupling reaction to be more economical and accessible, due to its utilization of an expensive and sensitive nickel mediator. Chapter 3 describes the Ni(COD)₂-free synthesis of high-surface area PAFs via the in-situ reduction of a more cost-effective Ni(II) source. Anhydrous nickel dibromide is reduced with activated zinc in the presence of COD and bipy to reach Ni(bipy)(COD), the reactive intermediate in the conventional Ni(COD)₂-mediated synthesis. The PAF produced through this route was comparable to PAF produced through the conventional synthesis. This route was generalizable to seven different monomers yielding polymers that were comparable in all but one case to those synthesized through Ni(COD)₂-mediated approaches. Additionally, the use of less sensitive reagents allowed for gram-plus scale syntheses on the Schlenk line, further increasing accessibility by eliminating the need for an inert atmosphere glovebox. Mesoporous PAFs have been a system of interest for many years. The inability to synthesize them through an isoreticular-expansion style approach has historically been attributed to interpenetration growing polymer network with other polymer strands, newly enabled by the larger pores. Chapter 4 presents an alternative hypothesis, that longer-strut POPs are more defective. The effects of defects in these systems were larger unknown until recently, it is conceivable that there may be more defects present in longer strut systems. Defectivity in long-strut materials is initially investigated using an extended PPN-4 system, PPN-4-XL. The lack of solubility of digested fragments led to the exploration of alternative alkyl substituted systems. Additionally, three other extended strut systems were synthesized and their properties are compared to the shorter-strut conventional examples. The inability to differentiate between interpenetrated and collapsed defective structures illustrates the need for the development of new imaging techniques that can resolve spatial differences in amorphous systems.

Purchased from AmBeed: 366-18-7

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 1~54

1
[ 366-18-7 ]
[ 13040-77-2 ]

References: [1]Journal of the Chinese Chemical Society,2003,vol. 50,p. 189 - 192.
[2]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1071 - 1077.
[3]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1071 - 1077.

2
[ 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.

3
[ 366-18-7 ]
H⁺ [ No CAS ]
[ 13040-77-2 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 4779 - 4782.

4
[ 366-18-7 ]
[ 22693-41-0 ]
[ 7646-85-7 ]
[ 112043-96-6 ]

References: [1]Inorganic Chemistry,1988,vol. 27,p. 493 - 496.

5
[ 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.

6
[ 366-18-7 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 1761-56-4 ]
[ 345914-37-6 ]

References: [1]Journal of Molecular Catalysis A: Chemical,2001,vol. 169,p. 41 - 45.

7
[ 366-18-7 ]
copper(II) perchlorate hexahydrate [ No CAS ]
[ 14257-84-2 ]
Cu⁽²⁺⁾*C₁₀H₈N₂*CH₃CONHCH(C₆H₅)CO₂^(1-)*ClO₄^(1-)*2H₂O = [Cu(C₁₀H₈N₂)(CH₃CONHCH(C₆H₅)CO₂)]ClO₄*2H₂O [ No CAS ]

References: [1]Polyhedron,1996,vol. 15,p. 1783 - 1791.

8
[ 366-18-7 ]
[ 5743-04-4 ]
[ 81-16-3 ]
Cd(2-aminonaphthalene-1-sulfonate)2(2,2'-bipyridine)2 [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2007,vol. 633,p. 615 - 620.

9
[ 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.

10
[ 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.

11
[ 366-18-7 ]
[ 27148-03-4 ]
silver nitrate [ No CAS ]
[ 954103-47-0 ]

References: [1]Journal of Molecular Structure,2007,vol. 841,p. 110 - 117.

12
[ 366-18-7 ]
[ 554-95-0 ]
[ 6147-53-1 ]
[ 174899-82-2 ]
(EMIm)[Co₂(trimesate)₄H₇(2,2′-bipyridyl)₂] [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 10334 - 10335.

13
[ 366-18-7 ]
copper(II) nitrate trihydrate [ No CAS ]
[ 943-80-6 ]
Cu⁽²⁺⁾*NH₂CH(CH₂C₆H₄NH₂)CO₂^(1-)*C₁₀H₈N₂*NO₃^(1-)*H₂O=[Cu(NH₂CH(CH₂C₆H₄NH₂)CO₂)(C₁₀H₈N₂)]NO₃*H₂O [ No CAS ]

References: [1]Inorganic Chemistry,1997,vol. 36,p. 576 - 583.

14
[ 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.

15
[ 366-18-7 ]
[ 5970-45-6 ]
[ 130-85-8 ]
[ 1095905-74-0 ]

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

16
[ 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.

17
[ 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 ]