4,4'-Bis(diethylmethylphosphonate)-2,2'-bipyridine

Base Information

• Chemical Name: 4,4'-Bis(diethylmethylphosphonate)-2,2'-bipyridine
• CAS No.: 176220-38-5
• Molecular Formula: C20H30N2O6P2
• Molecular Weight: 456.416
• Mol file: 176220-38-5.mol

Synonyms:Phosphonicacid, [[2,2'-bipyridine]-4,4'-diylbis(methylene)]bis-, tetraethyl ester (9CI);[[2,2'-Bipyridine]-4,4'-diylbis(methylene)]bis[phosphonic acid] tetraethylester;

Chemical Property of 4,4'-Bis(diethylmethylphosphonate)-2,2'-bipyridine

Chemical Property:

• Boiling Point: 594.461 °C at 760 mmHg
• PKA: 4.35±0.30(Predicted)
• Flash Point: 313.319 °C
• PSA: 116.46000
• Density: 1.202 g/cm³
• LogP: 5.67580

Purity/Quality:

99% ^*data from raw suppliers

4,4''-Bis(diethylmethylphosphonate)-2,2''-bipyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,4'-Bis(diethylmethylphosphonate)-2,2'-bipyridine

There total 14 articles about 4,4'-Bis(diethylmethylphosphonate)-2,2'-bipyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0,134457-15-1) + triethyl phosphite (122-52-1) → 4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine (176220-38-5)

Guidance literature:

at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ic4014976

Reference yield: 93.0%

4,4’-bis(chloromethyl)-2,2’-bipyridine (138219-98-4) + triethyl phosphite (122-52-1) → 4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine (176220-38-5)

Guidance literature:

at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.02.027

Reference yield: 64.0%

phosphonic acid diethyl ester (762-04-9) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0,134457-15-1) → 4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine (176220-38-5)

Guidance literature:

In chloroform; at 85 ℃; for 6h;

DOI:10.1002/chem.201703989

upstream raw materials:

triethyl phosphate

4,4'-bis(bromomethyl)-2,2'-bipyridine

triethyl phosphite

4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine

Downstream raw materials:

4,4'-bis((E)-2-(4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-p-N,N-dimethylaminophenylthiophen-3-yl)cyclopenten-1-yl)-5-methylthiophen-2-yl)vinyl)-2,2'-bipyridine

4,4'-bis((E)-2-(4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-enyl)-5-methylthiophen-2-yl)vinyl)-2,2'-bipyridine

C₅H₃NC₅H₃N[CHCHC₆H₃(CHCHC₆H₃(C(CH₃)3)2)2]2

4,4'-bis((E,E)-2-{4-[2-(4-pyridyl)vinyl]phenyl}vinyl)-2,2'-bipyridyl

Refernces

Synthesis and photo-physical properties of methoxy-substituted π-conjugated-2,2′-bipyridines

10.1016/j.tetlet.2010.02.027

The research explores the synthesis and photo-physical properties of new methoxy-substituted p-conjugated 2,20-bipyridines, which are nitrogen-containing organo-materials with applications in materials chemistry. The purpose of this study is to develop highly emissive materials in the visible region at room temperature, which could be potential ligands for metal coordination and have applications in light-emitting devices. The researchers used the Horner–Wordsworth–Emmons reaction to synthesize three new highly conjugated 2,20-bipyridines (3a–c). Key chemicals involved in the synthesis include 4,4-bis-chloromethyl-2,2-bipyridine (1a), lithium diisopropylamide (LDA), chlorotrimethylsilane, hexachloroethane, cesium fluoride, tetraethyl-2,2-bipyridine-4,4-diylbis(methylene)diphosphonate (2), and various methoxy-substituted benzaldehydes (6a–c). The synthesized compounds (3a–c) were characterized by NMR spectroscopy, elemental analysis, and LC–MS. The study found that these compounds exhibit strong emission in the visible region with quantum yields of 0.59, 0.70, and 0.73 for 3a, 3b, and 3c, respectively. The research concludes that the synthesized bipyridines show excellent emissive properties and potential for use in light-emitting devices, with further investigations ongoing in the laboratory.

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