Names | |
---|---|
Preferred IUPAC name 2-Ethenylpyridine | |
Other names 2-Vinylpyridine 2VP | |
Identifiers | |
3D model (JSmol) | |
104505 | |
ChemSpider | |
ECHA InfoCard | 100.002.618 |
EC Number |
|
PubChem CID | |
RTECS number |
|
UNII | |
UN number | 3073 |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C7H7N | |
Molar mass | 105.140 g·mol−1 |
Appearance | colorless liquid |
Density | 0.977 g/cm3 |
Melting point | −50 °C (−58 °F; 223 K) |
Boiling point | 158 °C (316 °F; 431 K) |
27.5 g/L | |
Vapor pressure | 96 hPa (72 mmHg) at 100 °C |
Acidity (pKa) | 4.98 |
Viscosity | 1.17 mPas |
Hazards | |
GHS labelling: | |
Danger | |
H226, H301, H302, H311, H314, H317, H331, H411 | |
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
Flash point | 48 °C (118 °F; 321 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Vinylpyridine is an organic compound with the formula CH2CHC5H4N. It is a derivative of pyridine with a vinyl group 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 polymers and as an intermediate in the chemical, pharmaceutical, dye, and photo industries. [1] Vinylpyridine is sensitive to polymerization. It may be stabilized with a polymerisation inhibitor such as tert-butylcatechol. Owing to its tendency to polymerize, samples are typically refrigerated.
It was first synthesized in 1887. A contemporary preparation entails condensation of 2-methylpyridine with formaldehyde, followed by dehydration 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 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. [1]
An alternative synthesis involves the reaction of acrylonitrile and acetylene below 130–140 ̊C in the presence of organocobalt compounds as a catalyst. [1] Acrylonitrile is the solvent for the reaction. [2]
2-Vinylpyridine is readily polymerized or copolymerized with styrene, butadiene, isobutylene, methyl methacrylate, and other compounds in the presence of radical, cationic, or anionic initiators. The homopolymer is soluble in organic solvents such as methanol and acetone, 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, styrene, and butadiene, for use as a tire-cord binder. The tire cord is treated first with a resorcinol-formaldehyde 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. [2]
Due to the electron-withdrawing effect of the ring nitrogen atom, 2-vinylpyridine adds nucleophiles such as methoxide, cyanide, hydrogen sulfide at the vinylic site to give addition products. The addition product of methanol to 2-vinylpyridine, 2-(2-methoxyethyl)pyridine is a veterinary anthelmintic. [1]
Treating 2-vinylpyridine with 4-pyridinecarbonitrile and hydrogen chloride gives 1-[2-(2-pyridyl)ethyl]-4-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, a pharmaceutical.
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sucrose and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.
Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.
Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.
Acrylonitrile butadiene styrene (ABS) (chemical formula (C8H8)x·(C4H6)y·(C3H3N)z ) is a common thermoplastic polymer. Its glass transition temperature is approximately 105 °C (221 °F). ABS is amorphous and therefore has no true melting point.
Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses.
In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are sometimes called bipolymers. Those obtained from three and four monomers are called terpolymers and quaterpolymers, respectively. Copolymers can be characterized by a variety of techniques such as NMR spectroscopy and size-exclusion chromatography to determine the molecular size, weight, properties, and composition of the material.
The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions. The Heck reaction is a way to substitute alkenes.
An isocyanide is an organic compound with the functional group –N+≡C−. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.
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).
n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.
Polybutadiene [butadiene rubber, BR] is a synthetic rubber. It offers high elasticity, high resistance to wear, good strength even without fillers, and excellent abrasion resistance when filled and vulcanized. "Polybutadiene" is a collective name for homopolymers formed from the polymerization of the monomer 1,3-butadiene. The IUPAC refers to polybutadiene as "poly(buta-1,3-diene)". Historically, an early generation of synthetic polybutadiene rubber produced in Germany by Bayer using sodium as a catalyst was known as "Buna rubber". Polybutadiene is typically crosslinked with sulphur, however, it has also been shown that it can be UV cured when bis-benzophenone additives are incorporated into the formulation.
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.
Solution polymerization is a method of industrial polymerization. In this procedure, a monomer is dissolved in a non-reactive solvent that contains a catalyst or initiator.
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.
In polymer chemistry, a comonomer refers to a polymerizable precursor to a copolymer aside from the principal monomer. In some cases, only small amounts of a comonomer are employed, in other cases substantial amounts of comonomers are used. Furthermore, in some cases, the comonomers are statistically incorporated within the polymer chain, whereas in other cases, they aggregate. The distribution of comonomers is referred to as the "blockiness" of a copolymer.
N,N′-Methylenebisacrylamide (MBAm or MBAA, colloquially "bis") is the organic compound with the formula CH2[NHC(O)CH=CH2]2. A colorless solid, this compound is a crosslinking agent in polyacrylamides, e.g., as used for SDS-PAGE.
Acrylonitrile styrene acrylate (ASA), also called acrylic styrene acrylonitrile, is an amorphous thermoplastic developed as an alternative to acrylonitrile butadiene styrene (ABS), that has improved weather resistance. It is an acrylate rubber-modified styrene acrylonitrile copolymer. It is used for general prototyping in 3D printing, where its UV resistance and mechanical properties make it an excellent material for use in fused filament fabrication printers, particularly for outdoor applications. ASA is also widely used in the automotive industry.
2-Ethyl-2-oxazoline (EtOx) is an oxazoline which is used particularly as a monomer for the cationic ring-opening polymerization to poly(2-alkyloxazoline)s. This type of polymers are under investigation as readily water-soluble and biocompatible materials for biomedical applications.
2-Methylglutaronitrile is the organic compound with the formula NCCH2CH2CH(CH3)CN. This dinitrile is obtained in the large-scale synthesis of adiponitrile. It is a colorless liquid with an unpleasant odor. It is the starting compound for the vitamin nicotinamide and for the diester dimethyl-2-methylglutarate and the ester amide methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, which are promoted as green solvents. 2-Methylglutaronitrile is chiral but is mainly encountered as the racemate. It is also used to make Dytek A.
Dimethylaminoethyl acrylate or DMAEA is an unsaturated carboxylic acid ester having a tertiary amino group. It is a colorless to yellowish, water-miscible liquid with a pungent, amine-like odor. DMAEA is an important acrylic monomer that gives basic properties to copolymers.