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4-Vinylpyridine

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CAS:100-43-6
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CAS:100-43-6
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CAS:100-43-6
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  • 2023-10-14
  • CAS:100-43-6
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  • 2023-09-06
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  • 4-Vinylpyridine
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  • 2023-08-26
  • CAS:100-43-6
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4-Vinylpyridine Basic information
Product Name:4-Vinylpyridine
Synonyms:Vinylpyridine,4-;4-Vinylpyridine, 96%, stab. with 100ppm hydroquinone;4-Vinylpyridine (stabilized with TBC);4-Vinylpyridine, stabilized, 95+%;4-Vinylpyridine, 95%, stabilized;1-(4-Pyridinyl)ethene;4-Vinylpyridine, Stab. With 100Ppm Hydroquinone;4-Vinylpyridine ,95% [stabilized with TBC]
CAS:100-43-6
MF:C7H7N
MW:105.14
EINECS:202-852-0
Product Categories:Organics;Monomers;Polymer Science;Vinyl Halides, Amines, Amides, and Other Vinyl Monomers
Mol File:100-43-6.mol
4-Vinylpyridine Structure
4-Vinylpyridine Chemical Properties
Melting point <25 °C
Boiling point 62-65 °C/15 mmHg (lit.)
density 0.975 g/mL at 25 °C (lit.)
vapor pressure 2.28hPa at 25℃
refractive index n20/D 1.549(lit.)
Fp 125 °F
storage temp. -20°C
solubility Chloroform, Methanol (Slightly)
form Liquid
pkapK1:5.62(+1) (25°C)
color Clear colorless to yellow-brown
Water Solubility 29 G/L (20 ºC)
BRN 104506
Exposure limitsACGIH: TWA 1 mg/m3
OSHA: TWA 2 mg/m3
NIOSH: IDLH 50 mg/m3; Ceiling 2 mg/m3
Stability:Stable. Incompatible with strong acids, strong oxidizing agents.
LogP1.36 at 20℃
CAS DataBase Reference100-43-6(CAS DataBase Reference)
NIST Chemistry ReferencePyridine, 4-ethenyl-(100-43-6)
EPA Substance Registry System4-Vinylpyridine (100-43-6)
Safety Information
Hazard Codes T
Risk Statements 10-25-34-42/43-23/25
Safety Statements 23-26-36/37/39-45-28A-16
RIDADR UN 3073 6.1/PG 2
WGK Germany 3
RTECS UU1045000
8-10
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29333990
Hazardous Substances Data100-43-6(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
4-Vinylpyridine Usage And Synthesis
Description4-vinylpyridine (4VP) is a pyridine derivative with a vinyl group in the 4-position. It is a colorless liquid, although impure samples are often brown. This compound belongs to a class of polar vinyl monomers that are important in many applications due to the ability of their polymers to form complexes of the electron-rich pyridine ring and to form polyelectrolytes through protonation or quaternization with alkyl or aryl halides. 4VP is sometimes used in biochemistry to alkylate protein cysteine residues. When compared to other alkylation agents, such as iodoacetamide, acrylamide, and N-ethylmaleimide, 4VP is less reactive, meaning the completion rate of cysteine alkylation is lower, but it also yields fewer side reactions[1].
Chemical Propertiesdark brown to yellow liquid. 2.9g can be dissolved in 100g of water at 20℃, soluble in methanol, ether, benzene, acetone, and slightly soluble in ether. When exposed to light and heat, polymerization occurs, and 0.1%-0.2% hydroquinone is often added as a polymerization inhibitor during storage.
Uses4-Vinylpyridine acts as a co-monomer in styrene-butadiene polymers to promote adhesion between the rubber compound and supporting fibers (or cords) in tires, belts and hoses. It serves as an intermediate for manufacturing chemicals and pharmaceuticals. Further, it is used as a reagent for the modification of cysteine. In addition to this, it is used to make poly(4-vinylpyridine) and elastomers.
Preparation4-Vinylpyridine is synthesized by reacting 4-picoline with formaldehyde to generate 4-pyridineethanol, which is then dehydrated.
Application4-Vinylpyridine was used as a monomer in polymer chemistry and induced nonimmunological contact urticaria and allergic contact dermatitis. No crossreactivity is observed between pyridine derivatives. It can be copolymerized with many other monomers, in particular cationic monomers, such as acrylamide, acrylates, and also with other vinyl-based monomers (e.g. styrene).?
Flammability and ExplosibilityFlammable
Purification Methods6 2 . Purify the monomer by fractional distillation under a good vacuum and in a N2 atmosphere and store it in sealed ampoules under N2, and keep it in the dark at -20o. The picrate has m 175-176o. [UV: Coleman & Fuoss J Am Chem Soc 77 5472 1955, Overberger et al. J Polymer Sci 27 381 1958, Petro & Smyth J Am Chem Soc 79 6142 1957.] It is used for alkylating SH groups in peptides [Anderson & Friedman Can J Biochem 49 1042 1971, Cawins & Friedman Anal Biochem 35 489 1970]. [Beilstein 20 II 170, 20 III/IV 2887, 20/6 V 213.]
References [1] Baskaran, D. and A. Müller. “Anionic Polymerization of Polar Vinyl Monomers.” (2012): 623-655
Tag:4-Vinylpyridine(100-43-6) Related Product Information
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