4,4'-Vinylenedipyridine

• CAS: 13362-78-2
• Catalog Number: ACM13362782-1
• Category: Main Products
• Molecular Weight: 182.22g/mol
• Molecular Formula: C12H10N2
• Synonyms: (E)-4,4'-Vinylenedipyridine;1,2-trans-(4-Pyridyl)ethene
• IUPAC Name: 4-[(E)-2-pyridin-4-ylethenyl]pyridine
• InChI: InChI=1S/C12H10N2/c1(11-3-7-13-8-4-11)2-12-5-9-14-10-6-12/h1-10H/b2-1+
• InChI Key: MGFJDEHFNMWYBD-OWOJBTEDSA-N
• Melting Point: >143 °C
• Appearance: Brown to Dark brown solid
• Complexity: 157
• CompoundIs Canonicalized: Yes
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• EC Number: 236-432-3;214-491-6
• Exact Mass: 182.084398327g/mol
• Formal Charge: 0
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 0
• Isotope Atom Count: 0
• Monoisotopic Mass: 182.084398327g/mol
• NSC Number: 11470
• Rotatable Bond Count: 2
• Topological Polar Surface Area: 25.8Ų
• Undefined Atom Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• XLogP3: 2.1

Case Study

Preparation of Inorganic-Organic Complex Compounds by in-situ Alkylation of 4,4'-Vinylenedipyridine

Cui, Jian-Qiu, et al. Journal of Inorganic and General Chemistry, 2017, 643(7), 483-487.

HgI2, 4,4'-vinylenedipyridine and HI undergo solvothermal reaction in an alcohol solution (methanol, ethanol or pentanol) to generate a class of organic-inorganic hybrid complexes. The organic cations were produced through the cleavage of the alcoholic C-O bond, followed by a one-step in situ N-alkylation of 4,4'-vinylenedipyridine under acidic conditions. This method offers a less toxic and more efficient alternative for synthesizing new organic cations compared to the conventional use of alkyl iodide as one of the reactants.
Synthesis procedure of organic Iodides/Iodidomercurates
· For the synthesis of [C14H16N2][I4]2-(1): In a Pyrex glass tube (15 cm in length and 2 cm in inner diameter), a mixture of HgI2 (0.068 g, 0.15 mmol), 4,4'-vinylenedipyridine (0.054 g, 0.3 mmol), HI (1.0 mL), methanol (1.5 mL), and acetonitrile (4.5 mL) was prepared. After stirring for 10 minutes, the mixture was sealed and heated in an oven at 150°C for 35 hours. It was then allowed to cool to room temperature for 3 days, resulting in the formation of purple-red crystals of 1, which were collected through filtration, washed with acetonitrile, and air-dried.
· For the synthesis of [C16H20N2][HgI4] (2): Yellow crystals of 2 were obtained using a procedure similar to that of 1, with the only difference being the substitution of methanol with ethanol (1.5 mL).
· For the synthesis of [C22H32N2][HgI4]4 (3): Red crystals of 3 were produced through a method akin to that of 1, but with pentanol (1.5 mL) replacing methanol.

Application of trans-4,4'-Vinylenedipyridine in the Preparation of Metallosupramolecular Polypseudorotaxane

Xia, Danyu, et al. Macromolecules, 2018, 51(7), 2716-2722.

A novel metallosupramolecular polypseudorotaxane that is responsive to three different stimuli was developed and synthesized. This structure combines a dual-responsive pillararene-based [2]pseudorotaxane with a cyanide-responsive copper(II) coordination. This marks the first instance of a pH-sensitive, pillararene-based polypseudorotaxane exhibiting sensitivity to pH, light, and cyanide, suggesting significant potential for applications in sensors, drug delivery systems, adaptive coatings, and more.
Synthesis steps of metallosupramolecular polypseudorotaxane
· The synthesis of the metallosupramolecular polypseudorotaxane involved several key steps. Initially, a new category of pH-sensitive pillar[5]arenes was created, specifically a morpholine-substituted pillar[5]arene (H).
· Subsequently, compound H was employed to form a dual-responsive [2]pseudorotaxane with a UV light-sensitive azastilbenzene derivative, trans-4,4'-vinylenedipyridine (trans-G).
· Lastly, the triple stimuli-responsive metallosupramolecular polypseudorotaxane was synthesized through the coordination of Cu(II) with the [2]pseudorotaxane, leveraging copper's abundance, cost-effectiveness, and strong binding affinity for pyridine groups.

Custom Q&A

What is the molecular formula of 4,4'-Vinylenedipyridine?

The molecular formula is C12H10N2.

What is the molecular weight of 4,4'-Vinylenedipyridine?

The molecular weight is 182.22 g/mol.

What is the IUPAC name of 4,4'-Vinylenedipyridine?

The IUPAC name is 4-[(E)-2-pyridin-4-ylethenyl]pyridine.

What is the InChI code of 4,4'-Vinylenedipyridine?

The InChI code is InChI=1S/C12H10N2/c1(11-3-7-13-8-4-11)2-12-5-9-14-10-6-12/h1-10H/b2-1+.

What is the CAS number of 4,4'-Vinylenedipyridine?

The CAS number is 13362-78-2.

What is the XLogP3-AA value of 4,4'-Vinylenedipyridine?

The XLogP3-AA value is 2.1.

How many hydrogen bond acceptor counts are there in 4,4'-Vinylenedipyridine?

There are 2 hydrogen bond acceptor counts.

What is the topological polar surface area of 4,4'-Vinylenedipyridine?

The topological polar surface area is 25.8Ų.

How many rotatable bond counts are there in 4,4'-Vinylenedipyridine?

The number of rotatable bond counts is not mentioned in the reference.

What is the physical description of 4,4'-Vinylenedipyridine?

It is described as a tan crystalline powder according to a source.