2-Vinylpyridine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula CH₂CHC₅H₄N. It is a derivative of

pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...

with a

vinyl group In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound contain ...

in the 2-position, next to the nitrogen. It is a colorless liquid, although samples are often brown. It is used industrially as a precursor to specialty

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

s and as an intermediate in the chemical, pharmaceutical, dye, and photo industries. Vinylpyridine is sensitive to polymerization. It may be stabilized with a free radical inhibitor such as ''tert''-butylcatechol. Owing to its tendency to polymerize, samples are typically refrigerated.

Synthesis

It was first synthesized in 1887. A contemporary preparation entails condensation of

2-methylpyridine 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. Synthesis 2 ...

with formaldehyde, followed by

dehydration In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...

of the intermediate alcohol. The reaction is carried out between 150–200 °C in an autoclave. The conversion is kept relatively low. After removal of unreacted 2-methylpyridine by distillation, concentrated aqueous

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

is added to the residue and the resultant mixture is distilled under reduced pressure. During distillation, the dehydration of 2-(2-pyridyl)ethanol occurs to give 2-vinylpyridine, which can be purified further by fractional distillation under reduced pressure in the presence of an inhibitor such as

4-tert-butylcatechol 4-''tert''-Butylcatechol (TBC) is an organic chemical compound which is a derivative of catechol. TBC is available in the form of a solid crystal flake and 85% solution in methanol or water. Uses It is added as a stabilizer and polymerisation ...

. :CH₃C₅H₄N + CH₂O → HOCH₂CH₂C₅H₄N :HOCH₂CH₂C₅H₄N → CH₂=CHC₅H₄N + H₂O An alternative synthesis involves the reaction of

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular ...

and

acetylene Acetylene (systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...

below 130–140 ̊C in the presence of

organocobalt compound Organocobalt chemistry is the chemistry of organometallic compounds containing a carbon to cobalt chemical bond. Organocobalt compounds are involved in several organic reactions and the important biomolecule vitamin B12 has a cobalt-carbon bond. ...

s as a catalyst. Acrylonitrile is the solvent for the reaction. :

Uses

Polymeric derivatives

2-Vinylpyridine is readily polymerized or copolymerized with

styrene Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...

butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...

isobutylene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Productio ...

methyl methacrylate Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA ...

, and other compounds in the presence of radical, cationic, or anionic initiators. The homopolymer is soluble in organic solvents such as

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

and

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

, whereas cross-linked copolymers are insoluble in organic solvents. An important application of 2-vinylpyridine involves the production of a latex terpolymer of 2-vinylpyridine,

, and

, for use as a tire-cord binder. The tire cord is treated first with a

resorcinol Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or '' meta''-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in w ...

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

polymer and then with a terpolymer made from 15% 2-vinylpyridine, styrene, and butadiene. This treatment gives the close bonding of tire cord to rubber. 2-Vinylpyridine is a co-monomer for acrylic fibers. Between 1–5% of copolymerized 2-vinylpyridine provide the reactive sites for dyes.Bönnemann, H.; Brijoux, W.. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. 2008, p. 188

Organic synthesis

Due to the electron-withdrawing effect of the ring nitrogen atom, 2-vinylpyridine adds

nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

s such as

methoxide In organic chemistry, methoxides are organic salts with a anion. They are the simplest alkoxides. Sodium methoxide and potassium methoxide have widespread use, though other metal-cation variants such as lithium methoxide, rubidium methoxide, ...

cyanide Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The unde ...

at the vinylic site to give addition products. The addition product of methanol to 2-vinylpyridine, 2-(2-methoxyethyl)pyridine is a veterinary

anthelmintic Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may a ...

. Treating 2-vinylpyridine with 4-pyridinecarbonitrile and

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

gives 1- -(2-pyridyl)ethyl4-cyanopyridinium chloride, which then can be used to prepare dimethylaminopyridine (DMAP), a widely used base catalyst. 2-Vinylpyridine is used in the production of

Axitinib Axitinib, sold under the brand name Inlyta, is a small molecule tyrosine kinase inhibitor developed by Pfizer. It has been shown to significantly inhibit growth of breast cancer in animal (xenograft) models and has shown partial responses in clini ...

, a pharmaceutical.

References

{{DEFAULTSORT:Vinylpyridine, 2- Pyridines Monomers Vinyl compounds

Synthesis

Uses

Polymeric derivatives

Organic synthesis

See also

References