1749-29-7

Basic information

• Product Name: (2-pyridylmethyl)lithium
• Synonyms: (2-pyridylmethyl)lithium
• CAS NO: 1749-29-7
• Molecular Formula: C₆H₆N*Li
• Molecular Weight: 99.05954
• EINECS: 217-134-2
• Mol File: 1749-29-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 127.5°Cat760mmHg
• Flash Point: 26.1°C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: (2-pyridylmethyl)lithium(CAS DataBase Reference)
• NIST Chemistry Reference: (2-pyridylmethyl)lithium(1749-29-7)
• EPA Substance Registry System: (2-pyridylmethyl)lithium(1749-29-7)

Safety Data

• Hazardous Substances Data: 1749-29-7(Hazardous Substances Data)

Usage

Description

(2-pyridylmethyl)lithium is a chemical compound that belongs to the class of organolithium reagents, which are commonly used in organic synthesis. It is derived from the reaction of 2-pyridylmethyl chloride with lithium metal. (2-pyridylmethyl)lithium is a strong nucleophile and a powerful base, making it useful for a variety of reactions such as nucleophilic substitutions and metalations. It is known for its ability to form carbon-carbon bonds and is often used to introduce the 2-pyridylmethyl group into organic molecules. (2-pyridylmethyl)lithium is a reactive and air-sensitive compound, requiring careful handling and storage in an inert atmosphere.

Uses

Used in Organic Synthesis:
(2-pyridylmethyl)lithium is used as a reagent for nucleophilic substitutions and metalations in organic synthesis. Its strong nucleophilic and basic properties enable it to participate in various chemical reactions, facilitating the formation of carbon-carbon bonds and the introduction of the 2-pyridylmethyl group into organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2-pyridylmethyl)lithium is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form carbon-carbon bonds and introduce the 2-pyridylmethyl group makes it a valuable tool in the development of new drugs and drug candidates.
Used in Chemical Research:
(2-pyridylmethyl)lithium is also used in chemical research as a versatile reagent for exploring new reaction pathways and mechanisms. Its strong nucleophilic and basic properties allow researchers to investigate a wide range of chemical transformations and develop new synthetic methods.
Used in Material Science:
In material science, (2-pyridylmethyl)lithium can be used as a precursor for the synthesis of novel materials with unique properties. Its ability to form carbon-carbon bonds and introduce the 2-pyridylmethyl group can contribute to the development of new materials with potential applications in various fields, such as electronics, energy storage, and catalysis.

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

Upstream product

• 109-06-8 α-picoline 
• 591-51-5 phenyllithium 
• 4111-54-0 lithium diisopropyl amide 
• 109-72-8 n-butyllithium 

Downstream Products

• 1132-37-2 bis(2-pyridyl)methane 
• 77429-58-4 tris(2-pyridyl)methane 
• 106989-75-7 rac-(E)-4-phenyl-1-(pyridin-2-yl)but-3-en-2-ol 
• 1620-53-7 1-phenyl-2-pyridin-2-ylethanone 
• 59576-32-8 1,2-di(pyridin-2-yl)ethanone 
• 59576-33-9 2-(2-pyridinyl)-1-(3-pyridinyl)ethanone 
• 72076-59-6 1-(4-methylphenyl)-2-(2-pyridinyl)-ethanone 
• 59576-34-0 2-(pyridin-2-yl)-1-(pyridin-4-yl)ethanone 
• 57476-56-9 1,7-di(2-pyridyl)heptane 
• 100398-32-1 2-(2'-pyrido)-2-chloroacetophenone 
• 109866-61-7 2-phenyl-1-piperidino-3-[2]pyridyl-propan-2-ol 
• 10420-99-2 1-(4-chlorophenyl)-2-(pyridin-2-yl)ethanone 
• 77035-44-0 α-cyano-2-pyridineacetonitrile 
• 6303-73-7 1-(pyridin-2-yl)-butan-2-one 

Relevant articles and documents

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

Neutral, formally Fe(iv) alkylidene species are sought as plausible olefin metathesis catalysts, and the synthesis of several is described herein. The complexes are prepared via nucleophilic attack (Nu = MeLi, PhCH2K, 2-picolyllithium, Me2PCH2Li, MePhPCH2Li, Ph2PCH2Li) at the imine of cationic [mer-{κ-C,N,C-(C6H4-yl)-2-CH=N(2-C6H4-C(iPr)=)}Fe(PMe3)3][B(3,5-CF3-C6H3)4]. In contrast, MeMgCl and mesityllithium displaced and deprotonated bound PMe3, respectively. Structural details are provided for mer-{κ-C,N,C-(C6H4-yl)-2-CH(Bn)N(2-C6H4-C(iPr)=)}Fe{trans-(PMe3)2}N2 and {κ-C,N,C,P-(C6H4-yl)-2-CH(CH2PMe2)N(2-C6H4-C(iPr)=)}Fe(PMe3)2.

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

The possibility of obtaining pyridylallene hydrocarbons with normal structure with a branched grouping in the side chain on the basis of vinyl(alkyl)acetylene hydrocarbons with iso structures and, respectively, 2-picolyl and 2,6-lutidyllithium is demonstrated.

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

The new pyridine-borane compound (2-picolyl)BCy2, readily prepared from 2-picolyllithium and ClBCy2, adopts a head-to-tail dimeric structure in the solid state as indicated by X-ray diffraction analysis and according to NMR and DFT studies, the dimeric form equilibrates in solution with a strained monomeric structure; the ambiphilic behavior of the new compound is illustrated by its bridging coordination to the (p-cymene)RuCl2 unit. The Royal Society of Chemistry.