4-Benzyl-2-methylpyridine

Base Information

• Chemical Name: 4-Benzyl-2-methylpyridine
• CAS No.: 7300-29-0
• Molecular Formula: C13H13 N
• Molecular Weight: 183.253
• European Community (EC) Number: 230-744-3
• DSSTox Substance ID: DTXSID40993760
• Nikkaji Number: J212.297I
• Wikidata: Q82984509
• Mol file: 7300-29-0.mol

Synonyms:4-benzyl-2-methylpyridine;7300-29-0;2-Picoline, 4-benzyl-;EINECS 230-744-3;SCHEMBL1563564;DTXSID40993760

Chemical Property of 4-Benzyl-2-methylpyridine

Chemical Property:

• Vapor Pressure: 0.00325mmHg at 25°C
• Boiling Point: 292.2°C at 760 mmHg
• Flash Point: 121.5°C
• PSA: 12.89000
• Density: 1.027g/cm³
• LogP: 2.98080
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 183.104799419
• Heavy Atom Count: 14
• Complexity: 161

Purity/Quality:

99% ^*data from raw suppliers

4-Benzyl-2-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=CC(=C1)CC2=CC=CC=C2

Technology Process of 4-Benzyl-2-methylpyridine

There total 13 articles about 4-Benzyl-2-methylpyridine 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: 95.0%

2-methyl-4-cyanopyridine (2214-53-1) + benzyltrimethylsilane (770-09-2) → 4-benzyl-2-methylpyridine (7300-29-0)

Guidance literature:

With 18-crown-6 ether; cesium fluoride; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.1c05764

Reference yield: 70.0%

benzyltrimethylsilane (770-09-2) + 2-methyl-4-(phenylsulfonyl)pyridine → 4-benzyl-2-methylpyridine (7300-29-0)

Guidance literature:

With 18-crown-6 ether; cesium fluoride; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.1c05764

Reference yield: 57.0%

4-bromo-2-methylpyridine (22282-99-1) + potassium benzyltrifluoroborate → 4-benzyl-2-methylpyridine (7300-29-0)

Guidance literature:

With 2,6-dimethylpyridine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; Ir(dF(CF₃)ppy)2(bpy)PF₆; 4,4'-di-tert-butyl-2,2'-bipyridine; In methanol; acetone; at 20 ℃; for 24h; Irradiation;

DOI:10.1126/science.1253647

upstream raw materials:

1-benzyl-2-methylpyridinium chloride

α-picoline

benzyl chloride

4-bromo-2-methylpyridine

Refernces

• 1、 Bandar, Jeffrey S.,Reidl, Tyler W.. "Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles". supporting information. p. 11939 - 11945. Retrieved 2021/08/20.
• 2、 Tellis, John C.,Primer, David N.,Molander, Gary A.. "Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis". . p. 433 - 436. Retrieved 2014/08/05.