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4-Vinylpyridine

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4-Vinylpyridine Basic information

Product Name:
4-Vinylpyridine
Synonyms:
  • 4-Ethenylpyridine
  • 4-vinylpyridine monomer
  • 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
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
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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.)
Flash point:
125 °F
storage temp. 
-20°C
form 
Liquid
pka
pK1:5.62(+1) (25°C)
color 
Clear colorless to yellow-brown
Water Solubility 
29 G/L (20 ºC)
BRN 
104506
Exposure limits
ACGIH: 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.
LogP
1.36 at 20℃
CAS DataBase Reference
100-43-6(CAS DataBase Reference)
NIST Chemistry Reference
Pyridine, 4-ethenyl-(100-43-6)
EPA Substance Registry System
4-Vinylpyridine (100-43-6)
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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 Data
100-43-6(Hazardous Substances Data)

MSDS

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4-Vinylpyridine Usage And Synthesis

Chemical Properties

dark 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.

Uses

4-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.

Application

4-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).?

Preparation

4-Vinylpyridine is synthesized by reacting 4-picoline with formaldehyde to generate 4-pyridineethanol, which is then dehydrated.

Flammability and Explosibility

Flammable

Purification Methods

6 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.]

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