2-Pyridyllithium

Base Information

• Chemical Name: 2-Pyridyllithium
• CAS No.: 17624-36-1
• Molecular Formula: C5H4 Li N
• Molecular Weight: 85.0345
• Hs Code.: 2933399090
• European Community (EC) Number: 241-600-4
• DSSTox Substance ID: DTXSID10170102
• Mol file: 17624-36-1.mol

Synonyms:2-Pyridyllithium;lithiopyridine;17624-36-1;lithium;2H-pyridin-2-ide;lithio pyridine;pyridinyllithium;Pyridyl lithium;2-lithiopyridine;2-pyridyl lithium;2-pyridyl-lithium;ortho-pyridyllithium;2-pyridinyl lithium;pyridin-2-yl lithium;DTXSID10170102;COHLMUXFVGVBKX-UHFFFAOYSA-N;EINECS 241-600-4;NS00087485

Chemical Property of 2-Pyridyllithium

Chemical Property:

• Vapor Pressure: 22.8mmHg at 25°C
• Boiling Point: 115.3°Cat760mmHg
• Flash Point: 20°C
• PSA: 12.36000
• Density: g/cm³
• LogP: 0.37950
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 85.05037757
• Heavy Atom Count: 7
• Complexity: 113

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].C1=CC=N[C-]=C1

Technology Process of 2-Pyridyllithium

There total 3 articles about 2-Pyridyllithium 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:

2-bromo-pyridine (109-04-6) → 2-pyridyllithium (17624-36-1)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; at -78 ℃;

DOI:10.1016/j.tet.2004.02.035

Reference yield:

2-bromo-pyridine (109-04-6) + n-butyllithium (109-72-8,29786-93-4) → 2-pyridyllithium (17624-36-1)

Guidance literature:

With diethyl ether; at -45 ℃;

DOI:10.1039/jr9500001039

Reference yield:

→ 2-pyridyllithium (17624-36-1) + 1-bromo-butane (109-65-9)

Guidance literature:

upstream raw materials:

2-bromo-pyridine

n-butyllithium

Downstream raw materials:

2,2'-dipyridyl ketone

pyridin-2-yl(pyridin-4-yl)methanone

1-(4-chlorophenyl)-1-(2-pyridyl)-1-propanol

phenylbis(pyridine-2-yl)methanol

Refernces

Preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives. Use of the chiral pool

10.1039/b000269k

The research focuses on the preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives, which are valuable in asymmetric catalysis. The experiments utilize naturally occurring chiral compounds such as D-mannitol, L-lactic acid, and L-mandelic acid as starting materials. Key reactants include 2-lithiopyridine, (R)-2,3-O-isopropylideneglyceraldehyde, and various esters derived from the aforementioned chiral compounds. The methodology involves the synthesis of 2-(1-hydroxyalkyl)pyridines and 6,6'-bis(1-hydroxyalkyl)-2,2'-bipyridines through a series of reactions, including lithiation, reduction with sodium borohydride, and nickel-catalyzed coupling. The analyses used to determine the success of the syntheses and the structures of the products encompass NMR spectroscopy (both 1H and 13C), optical rotation measurements, and in some cases, the preparation and analysis of Mosher's esters to determine the absolute configurations of the synthesized chiral alcohols.