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(2-pyridylmethyl)lithium


  • CasNo 1749-29-7
  • Purity 99%
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Cost-effective and customizable (2-pyridylmethyl)lithium 1749-29-7 factory

  • Molecular Formula: C6H6 N . Li
  • Molecular Weight: 99.0613
  • Boiling Point: 127.5°Cat760mmHg 
  • Flash Point: 26.1°C 
  • PSA: 12.36000 
  • Density: g/cm3 
  • LogP: 0.89310 

(2-pyridylmethyl)lithium(Cas 1749-29-7) Usage

General Description

(2-Pyridylmethyl)lithium, also known as 2-picolyllithium, is a reactive organolithium compound characterized by restricted methylene rotation, as evidenced by its high activation energy (~93 kJ mol-1 ) and entropy (~95 J K-1 mol-1 ). It serves as a nucleophile in synthetic chemistry, participating in reactions such as nucleophilic addition to imines in the formation of Fe(iv) alkylidene complexes. Additionally, it reacts with vinyl(tert-butyl)acetylene to yield pyridylallene derivatives. Its complexation behavior with lithium salts has been studied in both solid-state and solution phases, revealing dynamic structural changes in coordinating solvents.

InChI:InChI=1/C6H6N.Li/c1-6-4-2-3-5-7-6;/h2-5H,1H2;/rC6H6LiN/c7-5-6-3-1-2-4-8-6/h1-4H,5H2

1749-29-7 Relevant articles

Neutral Fe(iv) alkylidenes, including some that bind dinitrogen

Lindley, Brian M.,Jacobs, Brian P.,MacMillan, Samantha N.,Wolczanski, Peter T.

, p. 3891 - 3894 (2016)

Neutral, formally Fe(iv) alkylidene spec...

A DNMR Study of Restricted Methylene Rotation in 2-Pyridylmethyl- and 3-Methyl-2-pyridylmethyllithium

Matsui, Hideki,Yoshino, Akihiro,Yoshida, Tadayoshi,Takahashi, Kensuke

, p. 1052 - 1054 (1984)

Thermodynamical parameters for the restr...

-

Konishi et al.

, p. 2281 (1971)

-

Complexation behaviour of LiCl and LiPF6-model studies in the solid-state and in solution using a bidentate picolyl-based ligand

Espinosa-Jalapa, Noel Angel,Berg, Nele,Seidl, Michael,Shenderovich, Ilya G.,Gschwind, Ruth M.,Bauer, Jonathan O.

, p. 13335 - 13338 (2020)

Structural knowledge on ubiquitous lithi...

REACTION OF 2-PICOLYLLITHIUM AND 6-METHYL-2-PICOLYLLITHIUM WITH VINYL(tert-BUTYL)ACETYLENE

Cherkasov, L. N.

, p. 1181 - 1182 (1982)

The possibility of obtaining pyridylalle...

Synthesis, structure and coordination of the ambiphilic ligand (2-picolyl)BCy2

Vergnaud, Jerome,Ayed, Tahra,Hussein, Khansaa,Vendier, Laure,Grellier, Mary,Bouhadir, Ghenwa,Barthelat, Jean-Claude,Sabo-Etienne, Sylviane,Bourissou, Didier

, p. 2370 - 2372 (2008/02/04)

The new pyridine-borane compound (2-pico...

Carbon-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists

-

Page/Page column 28-29, (2008/06/13)

Disclosed are compounds of the formula o...

1749-29-7 Process route

α-picoline
109-06-8

α-picoline

2-pyridylmethyllithium
1749-29-7

2-pyridylmethyllithium

Conditions
Conditions Yield
With n-butyllithium; In hexane; pentane; at -30 - 20 ℃; for 2h; Inert atmosphere;
86%
With n-butyllithium; In diethyl ether; hexane; at -20 ℃;
48%
With phenyllithium; In diethyl ether; Ambient temperature; in an argon atmosphere;
With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1h;
With n-butyllithium; In hexane; for 2h; Ambient temperature;
With n-butyllithium; In diethyl ether; for 0.666667h; Heating / reflux;
With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.166667h;
α-picoline
109-06-8

α-picoline

n-butyllithium
109-72-8,29786-93-4

n-butyllithium

2-pyridylmethyllithium
1749-29-7

2-pyridylmethyllithium

Conditions
Conditions Yield
In diethyl ether; at -25 ℃; for 0.75h; Inert atmosphere;
52%
In tetrahydrofuran; hexanes; at -20 ℃; for 1.75h;

1749-29-7 Upstream products

  • 109-06-8
    109-06-8

    α-picoline

  • 591-51-5
    591-51-5

    phenyllithium

  • 4111-54-0
    4111-54-0

    lithium diisopropyl amide

  • 109-72-8
    109-72-8

    n-butyllithium

1749-29-7 Downstream products

  • 1132-37-2
    1132-37-2

    bis(2-pyridyl)methane

  • 77429-58-4
    77429-58-4

    tris(2-pyridyl)methane

  • 106989-75-7
    106989-75-7

    rac-(E)-4-phenyl-1-(pyridin-2-yl)but-3-en-2-ol

  • 1620-53-7
    1620-53-7

    1-phenyl-2-pyridin-2-ylethanone

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