2-Methyl-5-vinylpyridine

Base Information

• Chemical Name: 2-Methyl-5-vinylpyridine
• CAS No.: 140-76-1
• Deprecated CAS: 20260-76-8
• Molecular Formula: C8H9N
• Molecular Weight: 119.166
• Hs Code.: 2933399090
• European Community (EC) Number: 205-432-5
• UN Number: 2810,3073
• UNII: 34ET764YF8
• DSSTox Substance ID: DTXSID2059699
• Nikkaji Number: J38.338D
• Wikidata: Q27256361
• Mol file: 140-76-1.mol

Synonyms:2-methyl-5-vinylpyridine;2-methyl-5-vinylpyridine hydrochloride

Chemical Property of 2-Methyl-5-vinylpyridine

Chemical Property:

• Appearance/Colour: Clear to faintly opalescent liquid
• Vapor Pressure: 1.535mmHg at 25°C
• Melting Point: -12.0 °C
• Refractive Index: 1.555
• Boiling Point: 175.525 °C at 760 mmHg
• PKA: 5.58±0.10(Predicted)
• Flash Point: 56.618 °C
• PSA: 12.89000
• Density: 0.954 g/cm³
• LogP: 2.03300
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 119.073499291
• Heavy Atom Count: 9
• Complexity: 98.7
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

5-Ethenyl-2-methylpyridine 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC1=NC=C(C=C1)C=C
• Uses: Monomer for resins, oil additive, ore flotationagent, dye acceptor.

Technology Process of 2-Methyl-5-vinylpyridine

There total 15 articles about 2-Methyl-5-vinylpyridine 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: 99.0%

1-(6-methylpyridin-3-yl)ethanol maleate → 2-methyl-5-vinylpyridine (140-76-1,25038-86-2)

Guidance literature:

1-(6-methylpyridin-3-yl)ethanol maleate; With thionyl chloride; sodium hydroxide; In Isopropyl acetate;

With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; at 50 ℃; for 4h;

Reference yield: 47.0%

5-bromo-2-methylpyridine (3430-13-5) + tri-n-butyl(vinyl)tin (7486-35-3) → 2-methyl-5-vinylpyridine (140-76-1,25038-86-2)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 - 100 ℃; Inert atmosphere;

Reference yield:

5-ethyl-2-methyl-pyridine (104-90-5) → 2-methyl-5-vinylpyridine (140-76-1,25038-86-2) + pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + 5-ethyl-pyridine-2-carbonitrile (14178-13-3) + 2-cyano-5-vinylpyridine (63405-32-3)

Guidance literature:

With ammonia; water; oxygen; vanadia; titanium(IV) oxide; at 380 ℃; Further Variations:; reaction times; Product distribution;

DOI:10.1023/A:1020712212790

upstream raw materials:

5-ethyl-2-methyl-pyridine

2-methyl-5-formylpyridine

Methyltriphenylphosphonium bromide

5-bromo-2-methylpyridine

Downstream raw materials:

N-[2-(6-methyl-pyridin-3-yl)-ethyl]-aniline

N-methyl-N-[2-(6-methyl-[3]pyridyl)-ethyl]-aniline

2-Methyl-5-(2-methyl-cyclohex-3-enyl)-pyridine

2-Methyl-5-(5-methyl-cyclohex-3-enyl)-pyridine

Refernces

Asymmetric Syntheses of Amino Acids by Addition of Cyanide to the Schiff Bases in the Presence of Cyanide-Modified Hemin-Copolymer

10.1016/S0040-4039(01)80738-3

The research aimed to achieve asymmetric syntheses of amino acids through the addition of cyanide to Schiff bases in the presence of a cyanide-modified hemin-copolymer. The purpose was to enhance the optical yields of resulting amino acids by utilizing the steric control provided by the hemin-copolymer, which contains a large π electron system and shows aromatic properties. The study concluded that the optical yields (80-95% e.e.) were significantly higher than those obtained without the hemin-copolymer, indicating that the hemin in the copolymer provided strong steric control in the asymmetric addition of the CN group. Key chemicals used in the process included hemin, divinylbenzene, 2-methyl-5-vinylpyridine for the preparation of the hemin-copolymer, potassium cyanide for CN-modification, optically active amines such as (R)- and (S)-1-phenyl-1-ethylamine, (R)-1-phenyl-1-propylamine, and (R)-1-naphthyl-1-ethylamine, aliphatic aldehydes, and anhydrous sodium sulfate in the preparation of Schiff bases. The synthesized amino acids were then converted to N-trifluoroacetyl amino acid isopropyl esters for enantiomeric excess determination by gas chromatography using a chiral stationary phase.