2-Methylpyridine

Base Information

• Chemical Name: 2-Methylpyridine
• CAS No.: 109-06-8
• Deprecated CAS: 45505-34-8,82005-07-0,82005-07-0
• Molecular Formula: C6H7N
• Molecular Weight: 93.1283
• Hs Code.: 29333999
• European Community (EC) Number: 203-643-7,215-588-6
• ICSC Number: 0801
• NSC Number: 3409
• UN Number: 2313
• UNII: 3716Q16Q6A
• DSSTox Substance ID: DTXSID9021899
• Nikkaji Number: J5.087C
• Wikipedia: 2-Methylpyridine
• Wikidata: Q2216745
• Metabolomics Workbench ID: 52545
• ChEMBL ID: CHEMBL15732
• Mol file: 109-06-8.mol

Synonyms:2-methylpyridine;2-picoline;2-picolinium bromide

Chemical Property of 2-Methylpyridine

Chemical Property:

• Appearance/Colour: colourless to yellow liquid with an unpleasant smell
• Vapor Pressure: 10 mm Hg ( 24.4 °C)
• Melting Point: -70 °C(lit.)
• Refractive Index: n20/D 1.500(lit.)
• Boiling Point: 127.544 °C at 760 mmHg
• PKA: 5.97(at 20℃)
• Flash Point: 26.111 °C
• PSA: 12.89000
• Density: 0.94 g/cm³
• LogP: 1.39000
• Storage Temp.: Flammables area
• Sensitive.: Hygroscopic
• Solubility.: H2O: freely soluble
• Water Solubility.: MISCIBLE
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.057849228
• Heavy Atom Count: 7
• Complexity: 52.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2-Methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 10-20/21/22-36/37-24-20/22
• Safety Statements: 26-36-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC1=CC=CC=N1
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes and skin. The vapour is irritating to the respiratory tract. Exposure at high levels could cause unconsciousness.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• Uses: Solvent; intermediate in the dye and resins industries. 2-Picoline is used as an intermediate in agrochemicals and pharmaceuticals. It serves as a solvent as well as to prepare dyes and resins. It finds application as a constituent in cigarette smoke, bone oil, coal tar and coke oven emissions. Further, it acts as a precursor of 2-vinylpyridine, picolinic acid and nitrapyrin. It is also employed to study the electron and proton transfer reactions of lumiflavin. In addition, it is used in the synthetic pathway for the preparation of dearomatized, allylated and carbon-hydrogen bond activated pyridine derivatives. 2-Picoline is used as a reagent in the synthesis of 2-Picolineborane, a non-toxic alternative to sodium borohydride for the labelling of oligosaccharides.

Technology Process of 2-Methylpyridine

There total 238 articles about 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: 66.0%

pyridine-2-carbaldehyde (1121-60-4) → α-picoline (109-06-8) + 2-Hydroxymethylpyridine (586-98-1)

Guidance literature:

With hydrogen; GIPKh-105 copper-chromium catalyst; at 200 ℃; Product distribution; Mechanism; other isomeric pyridinecarboxaldehydes; var. temp.;

DOI:10.1007/BF01165032

Reference yield: 22.2%

pyridine (110-86-1) + methanol (67-56-1) → 2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6) + α-picoline (109-06-8) + picoline (108-89-4) + 2-Ethylpyridine (100-71-0) + 4-Ethylpyridine (536-75-4,151103-55-8) + 3-Methylpyridine (108-99-6)

Guidance literature:

Cs exchanged zeolite; at 450 ℃; Product distribution; investigation of the heterogeneous vapor-phase alkylation of pyridine with methanol over Na⁺, K⁺, Rb⁺, or Cs⁺ exchanged X- or Y-type zeolite in an atmosphere of nitrogen;

Reference yield: 0.3%

3-Methylpyridine (108-99-6) → pyridine (110-86-1) + α-picoline (109-06-8) + 2,3-Lutidine (583-61-9) + 2,4-lutidine (108-47-4) + 2,5-dimethylpyridine (589-93-5)

Guidance literature:

With hydrogen; aluminum oxide; nickel; at 330 ℃; under 750.06 Torr; Product distribution;

DOI:10.1007/BF00522129

upstream raw materials:

pyridine

methanol

lead(IV) tetraacetate

acetic acid

Downstream raw materials:

(E)-2-(2-(furan-2-yl)vinyl)pyridine

2,2'-dimethyl-1,1'-butanediyl-bis-pyridinium; dibromide

2-(3-phenylpropyl)pyridine

2-(1-phenethyl-3-phenyl-propyl)-pyridine

Refernces

• 1、 Yansone, D. P.,Stonkus, V. V.,Leitis, La. Ya.,Fleisher, M. B.,Shimanska, M.. "REACTIVITY OF ISOMERIC PYRIDINECARBOXALDEHYDES IN CATALYTIC HYDROGENATION". . p. 934 - 937. Retrieved 1994.
• 2、 Jordan, Richard F.,Taylor, Dennis F.. "Zirconium-Catalyzed Coupling of Propene and α-Picoline". . p. 778 - 779. Retrieved 1989.
• 3、 Boyington, Allyson J.,Riu, Martin-Louis Y.,Jui, Nathan T.. "Anti-Markovnikov Hydroarylation of Unactivated Olefins via Pyridyl Radical Intermediates". . p. 6582 - 6585. Retrieved 2017.
• 4、 Babudri et al.. "-". . p. 265,266,269. Retrieved 1979.
• 5、 Abronin, I. A.,Gorb, L. G.,Levin, D. Z.,Demidova, N. K.,Mortikov, E. S.. "QUANTUM - CHEMICAL AND EXPERIMENTAL STUDY OF CYCLOTRIMERIZATION OF ACETYLENE AND HETEROCYCLIZATION OF ACETYLENE WITH NITRILES". . p. 2317 - 2319. Retrieved 1982.
• 6、 García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.. "A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics". supporting information. . Retrieved 2022/01/04.
• 7、 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.