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517763

Sigma-Aldrich

2,2′-Bipyridine-5,5′-dicarboxylic acid

97%

Synonym(s):

6,6′-Binicotinic acid

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About This Item

Empirical Formula (Hill Notation):
C12H8N2O4
CAS Number:
1802-30-8
Molecular Weight:
244.20
MDL number:
MFCD01318320
UNSPSC Code:
12352100
PubChem Substance ID:
24873972
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

97%

mp

>360 °C (lit.)

functional group

carboxylic acid

SMILES string

OC(=O)c1ccc(nc1)-c2ccc(cn2)C(O)=O

InChI

1S/C12H8N2O4/c15-11(16)7-1-3-9(13-5-7)10-4-2-8(6-14-10)12(17)18/h1-6H,(H,15,16)(H,17,18)

InChI key

KVQMUHHSWICEIH-UHFFFAOYSA-N

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General description

2,2′-Bipyridine-5,5′-dicarboxylic acid also known as 6,6′-Binicotinic acid, is a versatile polypyridyl ligand commonly used in the synthesis of metal–organic frameworks.[1]

Application


  • Zn-MOFs Containing Pyridine and Bipyridine Carboxylate Organic Linkers and Open Zn2+ Sites: This study discusses the synthesis and characterization of Zinc-based Metal-Organic Frameworks (MOFs) utilizing 2,2′-Bipyridine-5,5′-dicarboxylic acid as a linker, showing potential applications in gas storage and separation (J Kim et al., 2015).

  • Ethylene oligomerization in metal organic frameworks bearing nickel (ii) 2, 2′-bipyridine complexes: Reports the use of 2,2′-Bipyridine-5,5′-dicarboxylic acid in Nickel-based MOFs for catalyzing ethylene oligomerization, highlighting the versatility of MOFs in catalysis (MI Gonzalez et al., 2017).

  • Two 3-D metal organic frameworks containing 2, 2′-bipyridine-5, 5′-dicarboxylic acid: synthesis, structure, and magnetic properties: Discusses the synthesis and magnetic properties of two 3-D MOFs built with 2,2′-Bipyridine-5,5′-dicarboxylic acid, demonstrating potential for advanced material applications (M Fang et al., 2014).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000360692
0000330395
0000215231
0000213647
0000197914

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Synthesis and properties of polyamides and polyesters on the basis of 2, 2'-bipyridine-5, 5'-dicarboxylic acid and the corresponding polymer-ruthenium complexes.
Yu SC, et al.
Macromolecules, 33(9), 3259-3273 (2000)
2, 2'-Bipyridine-5, 5'-dicarboxylic acid.
Wang C.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 65(9), o2081-o2081 (2009)
Woo Hyeong Sim et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 8(1), 2002144-2002144 (2021-01-14)
Lithium (Li) metal has attracted significant attention as next-generation anode material owing to its high theoretical specific capacity and low potential. For enabling the practical application of Li-metal as an anode according to energy demands, suppressing dendrite growth by controlling
N J Hales et al.
Journal of medicinal chemistry, 36(24), 3853-3858 (1993-11-26)
Members of a series of 2,2'-bipyridines have been synthesized and tested as inhibitors of prolyl hydroxylase (EC 1.14.11.2). The structure-activity relationships seen with [2,2'-bipyridine]-5-carboxylic acid (4) closely resemble those of pyridine-2-carboxylic acid (2). Accordingly, [2,2'-bipyridine]-5,5'-dicarboxylic acid (11, IC50 = 0.19
Ruthenium (II) complexes of 2, 2?-bipyridine-5, 5?-dicarboxylic acid: Synthesis, structure, DNA binding, cytotoxicity and antioxidant activity
amatchi TS, et al.
Inorganica chimica acta, 404, 58-67 (2013)
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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