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

solubility 

Chloroform, Methanol (Slightly)

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)

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

F 

8-10

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29333990

Hazardous Substances Data

100-43-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Vinylpyridine Usage And Synthesis

Description

4-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 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.

Reactions

4-Vinylpyridine belongs to a class of polar vinyl monomers with high electron affinity and can be used to synthesize poly(4-vinylpyridine) (P4VP). Its polymers are able to form complexes with electron-rich pyridine rings and can form polyelectrolytes by protonation or quaternization with alkyl or aryl halides. Anionic polymerization of vinylpyridine has been reported to undergo side reactions in both polar and nonpolar solvents, with the main side reaction being the attack of the anion on the pyridine ring of the monomer or polymer. In addition, bromate supported on P4VP in nonaqueous solutions has been used for the bromination of aromatic compounds with potassium bromide, a simple, efficient, mild, and selective method for methoxyaromatics, aniline, and phenol.

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.]

References

[1] Baskaran, D. and A. Müller. “Anionic Polymerization of Polar Vinyl Monomers.” (2012): 623-655

4-Vinylpyridine(100-43-6)Related Product Information

• Triethoxyvinylsilane
• Vinylmagnesium bromide
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• VINYL PROPIONATE
• Vinyl resin
• POLY(4-VINYLPYRIDINE)
• Silicone rubber,methyl-vinyl
• alpha-Vinylpyridine,2-VINYLPYRIDINE
• Vinyl ester resin
• 1,2-BIS(2-PYRIDYL)ETHYLENE
• CYANINE
• 1,1'-DIETHYL-4,4'-CARBOCYANINE IODIDE
• 4-Pyridineacrylic acid
• N-Vinyl-2-pyrrolidone
• 4-(1-NAPHTHYLVINYL)PYRIDINE
• 3-(2-NITROETHENYL)PYRIDINE
• POLY(4-VINYLPYRIDINE) SULFUR TRIOXIDE COMPLEX
• F16