2-Methylpyridine

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2-Methylpyridine
2-methylpyridine-2D-skeletal.png
2-methylpyridine-3D-balls.png
Names
Preferred IUPAC name
2-Methylpyridine
Other names
2-Picoline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.313
Properties
C6H7N
Molar mass 93.13 g/mol
Appearance Faintly yellow-green clear liquid
Density 0.943 g/mL
Melting point −70 °C (−94 °F; 203 K)
Boiling point 128 to 129 °C (262 to 264 °F; 401 to 402 K)
Miscible
-60.3·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2-Methylpyridine, or 2-picoline, is the compound described with formula C6H7N. 2-Picoline is a colorless liquid that has an unpleasant odor similar to pyridine. It is mainly used to make vinylpyridine and the agrichemical nitrapyrin.[1]

Synthesis[edit]

2-Picoline was the first pyridine compound reported to be isolated in pure form. It was isolated from coal tar in 1846 by T. Anderson.[2] It is now mainly produced by two principal routes, the condensation of acetaldehyde, formaldehyde, and ammonia and the cyclization of nitriles and acetylene. One example of such reaction is the combination of acetaldehyde and ammonia:

Synthesis of 2-picoline.png

Approximately 8000 t/a was produced worldwide in 1989.[3]

Reactions[edit]

Most of the reactions of picoline are centered on the methyl group. For example, the principal use of 2-picoline is as a precursor of 2-vinylpyridine. The conversion is achieved by condensation with formaldehyde:

2-Vinylpyridine from 2-picoline.png

The copolymer of 2-vinylpyridine, butadiene and styrene is used as an adhesive for textile tire cord. 2-Picoline is also a precursor to the agrichemical, nitrapyrin, which prevents loss of ammonia from fertilizers. Oxidation by potassium permanganate affords picolinic acid:[3]

Oxidation of 2-picoline.png

Deprotonation with butyllithium affords C5H4NCH2Li, a versatile nucleophile.[4]

Biodegradation[edit]

Like other pyridine derivatives, 2-methylpyridine is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. The compound is readily degradable by certain microorganisms, such as Arthrobacter sp. strain R1 (ATTC strain number 49987), which was isolated from an aquifer contaminated with a complex mixture of pyridine derivatives.[5] Arthrobacter and closely related Actinobacteria are often found associated with degradation of pyridine derivatives and other nitrogen heterocyclic compounds. 2-methypyridine and 4-methypyridine are more readily degraded and exhibit less volatilization loss from environmental samples than does 3-methypyridine.[6]

Drugs[edit]

  1. N-alkylation of picoline is used in production of amprolium, an antiprotozoan.
  2. Picoplatin is also N-alkylated.
  3. Dimethindene
  4. Encainide
  5. Butoprozine (butoprizine)

References[edit]

  1. ^ Eric F. V. Scriven, Ramiah Murugan. 'Pyridine and Pyridine Derivatives', Kirk-Othmer Encyclopedia of Chemical Technology, (2005). doi:10.1002/0471238961.1625180919031809.a01.pub2
  2. ^ Anderson, T. (1846). "On the constitution and properties of Picoline, a new organic base from Coal Tar" (Free full text at Google Books). Edinburgh New Phil. J. XLI: 146–156; 291–300. 
  3. ^ a b Shinkichi Shimizu; Nanao Watanabe; Toshiaki Kataoka; Takayuki Shoji; Nobuyuki Abe; Sinji Morishita; Hisao Ichimura. (2002). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a22_399. 
  4. ^ Stephanie Ganssl; Julia Pedronil; Alexandre Lumbrosol; Günther Leonhardt-Lutterbeckl; Antje Meißnerl; Siping Weil; Hans-Joachim Drexlerl; Detlef Hellerl; Bernhard Breital (2016). "􀀉􀀓􀀙􀀏􀀔􀀞􀀗􀀣􀀃􀀌􀀝􀀌􀀖􀀡􀀢􀀐􀀏􀀁􀀂􀀏􀀏􀀔􀀝􀀔􀀙􀀘􀀁􀀙􀀑􀀁􀀃􀀌􀀛􀀍􀀙􀀠􀀡􀀖􀀔􀀎􀀁􀀂􀀎􀀔􀀏􀀜􀀁􀀝􀀙􀀁􀀉􀀓􀀙􀀏􀀔􀀞􀀗􀀣􀀃􀀌􀀝􀀌􀀖􀀡􀀢􀀐􀀏􀀁􀀂􀀏􀀏􀀔􀀝􀀔􀀙􀀘􀀁􀀙􀀑􀀁􀀃􀀌􀀛􀀍􀀙􀀠􀀡􀀖􀀔􀀎􀀁􀀂􀀎􀀔􀀏􀀜􀀁􀀝􀀙􀀁Rhodium-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z-Enol Esters􀀊􀀐􀀛􀀗􀀔􀀘􀀌􀀖􀀁􀀂􀀖􀀕􀀡􀀘􀀐􀀜􀀁􀀝􀀙􀀟􀀌􀀛􀀏􀀜􀀁􀀁􀀣􀀅􀀘􀀙􀀖􀀁􀀅􀀜􀀝􀀐􀀊􀀐􀀛􀀗􀀔􀀘􀀌􀀖􀀁􀀂􀀖􀀕􀀡􀀘􀀐􀀜􀀁􀀝􀀙􀀟􀀌􀀛􀀏􀀜􀀁􀀁􀀣􀀅􀀘􀀙􀀖􀀁􀀅􀀜􀀝􀀐􀀛􀀜􀀁". Org. Synth. 93: 367–384. doi:10.15227/orgsyn.093.0367. 
  5. ^ O'Loughlin, E. J., G.K. Sims, and S.J. Traina. 1999. Biodegradation of 2-methyl, 2-ethyl, and 2-hydroxypyridine by an Arthrobacter sp. isolated from subsurface sediment. Biodegradation 10:93-104.
  6. ^ Sims, G.K.; L.E. Sommers (1985). "Biodegradation of pyridine derivatives in soil suspensions". Environmental Toxicology and Chemistry. 5: 503–509. doi:10.1002/etc.5620050601.