2456-81-7 Usage
Description
4-Pyrrolidinopyridine, a pyridine derivative, is a white to light brown crystalline mass known for its versatile applications in various chemical processes. It is characterized by its ability to act as a catalyst in polymerization reactions and as a ligand in metal complexes, making it a valuable compound in the field of chemistry.
Uses
Used in Polymerization Industry:
4-Pyrrolidinopyridine is used as a catalyst for polymerization reactions, specifically for the geometry-selective (E-selective) acylation of tetrasubstituted α, α'-alkenediols. Its role in these reactions contributes to the production of polymers with desired properties and characteristics.
Used in Metal Complexes:
In the field of coordination chemistry, 4-Pyrrolidinopyridine is used as a ligand in metal complexes, such as the Chloride and pseudohalide hydride-carbonyl ruthenium(II) complexes. Its presence in these complexes enhances their stability and reactivity, making it an essential component in the synthesis of various metal-based compounds.
Used as a Hypernucleophilic Acylation Catalyst:
4-Pyrrolidinopyridine also serves as a hypernucleophilic acylation catalyst, further expanding its applications in the realm of organic chemistry. This property allows it to facilitate a range of chemical reactions, contributing to the synthesis of complex organic molecules and compounds.
Synthesis Reference(s)
Synthetic Communications, 9, p. 251, 1979 DOI: 10.1080/00397917908064147Synthesis, p. 985, 1988 DOI: 10.1055/s-1988-27777
References
http://www.sigmaaldrich.com/catalog/product/aldrich/213373?lang=en®ion=US
http://www.sigmaaldrich.com/catalog/product/sial/83275?lang=en®ion=US
Yamanaka M et al. "Origin of High E -Selectivity in 4-Pyrrolidinopyridine-Catalyzed Tetrasubstituted α,α′-Alkenediol: A Computational and Experimental Study." Journal of Organic Chemistry 80.6(2015):3075-82.
J. G. Ma?ecki, and A. Maroń. "Chloride and pseudohalide hydride-carbonyl ruthenium(II) complexes with 4-pyrrolidinopyridine as co-ligand."Transition Metal Chemistry 38.2(2013):133-142.
Check Digit Verification of cas no
The CAS Registry Mumber 2456-81-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,5 and 6 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2456-81:
(6*2)+(5*4)+(4*5)+(3*6)+(2*8)+(1*1)=87
87 % 10 = 7
So 2456-81-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H12N2/c1-2-8-11(7-1)9-3-5-10-6-4-9/h3-6H,1-2,7-8H2/p+1
2456-81-7Relevant articles and documents
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Pedersen,Carlsen
, p. 844 (1978)
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Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime
Yuan, Chunling,Zhang, Lei,Zhao, Yingdai
, (2019/11/28)
We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.
Structures, Lewis Acidities, Electrophilicities, and Protecting Group Abilities of Phenylfluorenylium and Tritylium Ions
Follet, Elsa,Mayer, Peter,Berionni, Guillaume
supporting information, p. 623 - 630 (2017/01/18)
The isolation, characterization, and the first X-ray structures of a fluorenylium ion and its Lewis adducts with nitrogen- and phosphorus-centered Lewis bases are reported. Kinetics of the reactions of a series of fluorenylium ions with reference π-, σ-, and n-nucleophiles of various sizes and nucleophilicities allowed the interplay between electronic and structural parameters on the electrophilicities of these planarized tertiary carbenium ions to be elucidated. Structure–reactivity correlations and extensive comparisons of their reactivities with those of di- and triarylcarbenium ions are described. Quantitative determination of the electrofugalities of fluorenylium ions revealed to which extent they are complementing tritylium ions as protecting groups and how their tuning is possible. Determination of the equilibrium constants of the Lewis adducts formation between pyridines of calibrated Lewis basicities and phenylfluorenylium and tritylium ions allowed the determination of their Lewis acidities and to showcase the potential of these carbon-centered Lewis acids in catalysis.