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4-Vinylpyridine structure

4-Vinylpyridine
  • CAS：100-43-6
  • MW:105.13718
  • MF：C7H7N
4-Vinylpyridine, with the chemical formula C7H7N and CAS registry number 100-43-6, is a compound used in the synthesis of polymers and pharmaceuticals. This colorless liquid, also known as 4-Pyridinylethylene, is characterized by its vinyl group attached to the pyridine ring. It serves as a precursor in the production of various polymers like poly(4-vinylpyridine) and is utilized in the synthesis of pharmaceuticals and agrochemicals. 4-Vinylpyridine is a valuable compound in organic chemistry, finding applications in cross-coupling reactions and as a ligand in coordination chemistry. 4-Vinyl pyridine was used as a monomer in polymerchemistry and induced contact urticaria and contactdermatitis. It has been studied for its role in polymerization processes and as a monomer in the production of copolymers. Additionally, 4-Vinylpyridine has applications in the development of adhesives and coatings, contributing to advancements in material science and industrial chemistry. View more+
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1. Names and Identifiers
1.1 Name
4-Vinylpyridine
1.2 Synonyms
1-(4-Pyridinyl)ethene; 4-Ethenylpyridine; 4-Vinylpyridine (stabilized with TBC); 4-vinylpyridine monomer; 4-Vinylpyridine,stabilized; EINECS 202-852-0; MFCD00006447; Pyridine, 4-ethenyl-; Pyridine, 4-vinyl-; T6NJ D1U1; Vinylpyridine,4-; Γ-Vinylpyridine;
1.3 CAS No.
100-43-6
1.4 CID
7502
1.5 EINECS
202-852-0
1.6 Molecular Formula
C7H7N
1.7 Inchi
InChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2
1.8 InChkey
KFDVPJUYSDEJTH-UHFFFAOYSA-N
1.9 Canonical Smiles
C=CC1=CC=NC=C1
1.10 Isomers Smiles
C=CC1=CC=NC=C1
2. Properties
2.1 Solubility
29 G/L (20 ºC)
2.2 Appearance
Clear colorless to yellow-brown Liquid
2.3 Storage
Store at -20°C.
2.4 Chemical Properties
dark brown to yellow liquid
2.5 Color/Form
RED TO DARK BROWN LIQUID
2.6 Contact Allergens
4-Vinyl pyridine was used as a monomer in polymerchemistry and induced nonimmunological contacturticaria and allergic contact dermatitis. No crossreactivityis observed between pyridine derivatives.
2.7 Decomposition
DECOMPOSITION BY HEAT IS ACCOMPANIED BY RELEASE OF DANGEROUS CYANIDE FUMES.
2.8 Odor
Pungent unpleasant odor
2.9 Odor Threshold
AT ... CONCN ... /ABOVE 0.5 PPM 4-VINYLPYRIDINE HAS/ A VERY UNPLEASANT NAUSEATING ODOR. THE UNPLEASANT ODOR CAN BE TOLERATED @ CONCN THAT WILL PRODUCE ACUTE SYMPTOMS & IRRITATIONS.
2.10 pKa
pK1:5.62(+1) (25°C)
2.11 Water Solubility
H2O: 29 G/L (20 oC)
2.12 Spectral Properties
INDEX OF REFRACTION: 1.5449 @ 20 DEG C/D; MAX ABSORPTION (ALC): 242.5 NM (LOG E= 4.12); SADTLER REF NUMBER: 1249 (IR, PRISM)
IR: 5826 (Coblentz Society Spectral Collection)
UV: 6-110 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 155 (Varian Associates NMR Spectra Catalogue)
MASS: 471 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
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2.13 Stability
Stable. Incompatible with strong acids, strong oxidizing agents.
2.14 StorageTemp
-20°C
3. Use and Manufacturing
3.1 Description
4-Vinylpyridine (CAS 100-43-6) is a colorless to yellow liquid with a pungent odor. Its basic structure consists of a pyridine ring with a vinyl group attached to the 4-position. This chemical is soluble in water, alcohol, and ether. It has a boiling point of 115-116°C and a density of 0.98 g/mL. 4-Vinylpyridine is highly reactive and can undergo polymerization and addition reactions.

Applicable Fields
4-Vinylpyridine has various applications in different fields:

Chemical Industry: In the chemical industry, 4-vinylpyridine is used as a monomer for the synthesis of polymers and copolymers. It can undergo radical polymerization to form poly(4-vinylpyridine), which has applications in coatings, adhesives, and ion-exchange resins.

Pharmaceutical Industry: In the pharmaceutical industry, 4-vinylpyridine is used as a building block for the synthesis of various pharmaceutical compounds. It can be used to introduce functional groups or modify existing molecules.

Research and Development: 4-Vinylpyridine is also used in research and development laboratories as a reagent for various chemical reactions. It can participate in nucleophilic substitution reactions, addition reactions, and polymerization reactions.

Storage Conditions
Store in a cool, dry place.
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3.2 Methods of Manufacturing
Gamma-picoline + formaldehyde (condensation/dehydration)|...manufactured by treatment of 4-methylpyridine with aqueous formaldehyde, followed by dehydration of the resulting intermediate alcohol. The reaction of 2-vinylpyridine is carried out at 150 to 200 °C in an autoclave. 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 as a distillate, which can be purified further by fractional distillation under reduced pressure in the presence of an inhibitor such as 4-tert-butylcatecohol. 4-Vinylpyridine is manufactured by a similar method as that reported for 2-vinylpyridine.
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3.3 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.] 4-Vinylpyridine Preparation Products And Raw materials Preparation Products
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3.4 Usage
4-Vinyl pyridine was used as a monomer in polymerchemistry and induced contact urticaria and contactdermatitis.
4. Safety and Handling
4.1 Other Preventative Measures
ALL OPERATIONS INVOLVING HANDLING...SHOULD BE CONDUCTED IN WELL-VENTILATED CONDITIONS; PROCESS PLANT SHOULD...BE ENCLOSED & FITTED WITH LOCAL EXHAUST VENTILATION.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
ACUTE TOXICITY INFORMATION ON ANIMALS & EXPERIENCE WITH INTERMITTENT EXPOSURES IN MAN SHOW THAT MORE THAN ORDINARY CARE IS NEEDED TO AVOID SKIN CONTACT & INHALATION.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
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4.2 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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4.3 DOT Emergency Guidelines
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Fire: CAUTION: All these products have a very low flash point. Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Spill or Leak: Fully encapsulating, vapor protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Small spills: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Vinylpyridines, inhibited; Vinylpyridines, stabilized/
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4.4 FirePotential
Fire hazard is moderate ... .
4.5 Protective Equipment and Clothing
BRIEF EXPOSURES TO UNDETERMINED CONCN OF ... 4-VINYLPYRIDINE DURING LAB USE ... CAUSED EYE, NOSE & THROAT IRRITATION ... .
4.6 Report

Reported in EPA TSCA Inventory.

4.7 Skin, Eye, and Respiratory Irritations
BRIEF EXPOSURES TO UNDETERMINED CONCN OF ... 4-VINYLPYRIDINE DURING LAB USE ... CAUSED EYE, NOSE & THROAT IRRITATION ... .
4.8 Safety

Poison by ingestion. Slightly toxic by inhalation. A combustible liquid. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes: T
Risk Statements: 10-25-34-42/43-23/25
R10:  Flammable
R25:  Toxic if swallowed
R34:  Causes burns 
R42/43:  May cause sensitization by inhalation and skin contact 
R23/25:  Toxic by inhalation and if swallowed
Safety Statements: 23-26-36/37/39-45-28-16
S23:  Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 
S26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
S36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
S45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
S28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 
S16:  Keep away from sources of ignition - No smoking  
RIDADR: UN 3073 6.1/PG 2
WGK Germany: 3
RTECS: UU1045000
HazardClass: 6.1
PackingGroup of 4-Vinylpyridine (CAS NO.100-43-6): II

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4.9 Specification

  4-Vinylpyridine (CAS NO.100-43-6), its Synonyms are 4-Ethenylpyridine ; Pyridine, 4-ethenyl- ; Pyridine, 4-vinyl- ; gamma-Vinylpyridine .

4.10 Toxicity
Oral-rat LD50: 100 mg/kg; Oral-Mouse LD50: 161 mg/kg
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Skin corrosion, Category 1B

Skin sensitization, Category 1

Serious eye damage, Category 1

Acute toxicity - Inhalation, Category 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H226 Flammable liquid and vapour

H301 Toxic if swallowed

H311 Toxic in contact with skin

H314 Causes severe skin burns and eye damage

H317 May cause an allergic skin reaction

H331 Toxic if inhaled

H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P271 Use only outdoors or in a well-ventilated area.

P273 Avoid release to the environment.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P361+P364 Take off immediately all contaminated clothing and wash it before reuse.

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P311 Call a POISON CENTER/doctor/\u2026

P391 Collect spillage.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in CDCl3  
1H NMR : parameter in CCl4  
IR : CCl4 solution  
IR : liquid film  
Mass  
7. Synthesis Route
100-43-6Total: 14 Synthesis Route
 
108-89-4
108-89-4 95 Suppliers
 
100-43-6
100-43-6 43 Suppliers
 
872-85-5
872-85-5 293 Suppliers
 
100-43-6
100-43-6 43 Suppliers
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8. Precursor and Product
precursor:
872-85-5
872-85-5
5344-27-4
5344-27-4
108-89-4
108-89-4
50-00-0
50-00-0
28148-48-3
28148-48-3
34064-35-2
34064-35-2
497914-04-2
497914-04-2
400759-02-6
400759-02-6
67-56-1
67-56-1
product:
872-85-5
872-85-5
1453-82-3
1453-82-3
90134-00-2
90134-00-2
6926-71-2
6926-71-2
13258-63-4
13258-63-4
2127-05-1
2127-05-1
100-48-1
100-48-1
55-22-1
55-22-1
21351-43-9
21351-43-9
536-75-4
536-75-4
9. Computed Properties
10.Other Information
Usage
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.
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BRN
104506
Chemical Properties
dark brown to yellow liquid
Uses
4-Vinyl pyridine was used as a monomer in polymer chemistry and induced contact urticaria and contact dermatitis.
Contact allergens
4-Vinyl pyridine was used as a monomer in polymer chemistry and induced nonimmunological contact urticaria and allergic contact dermatitis. No crossreactivity is observed between pyridine derivatives.
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.]
View all
Storage Conditions
Gamma-picoline + formaldehyde (condensation/dehydration)|...manufactured by treatment of 4-methylpyridine with aqueous formaldehyde, followed by dehydration of the resulting intermediate alcohol. The reaction of 2-vinylpyridine is carried out at 150 to 200 °C in an autoclave. 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 as a distillate, which can be purified further by fractional distillation under reduced pressure in the presence of an inhibitor such as 4-tert-butylcatecohol. 4-Vinylpyridine is manufactured by a similar method as that reported for 2-vinylpyridine.
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Dissociation Constants
pKa= 5.62 (conjugate acid)
Experimental Properties
CONVERSION FACTORS: 1 MG/L IS EQUIVALENT TO 233 PPM, 1 PPM IS EQUIVALENT TO 4.3 MG/CU M|Dissolves in water to extent of 2.5%; water dissolves in it to 15%; soluble in dilute acids, hydrocarbons, alcohols, ketones, esters. Commercial material contains inhibitor. Combustible. /Vinylpyridine/
Storage features
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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Personal Protective Equipment
Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/
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Fire Potential
Fire hazard is moderate ... .
Preventive Measures
ALL OPERATIONS INVOLVING HANDLING...SHOULD BE CONDUCTED IN WELL-VENTILATED CONDITIONS; PROCESS PLANT SHOULD...BE ENCLOSED & FITTED WITH LOCAL EXHAUST VENTILATION.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|ACUTE TOXICITY INFORMATION ON ANIMALS & EXPERIENCE WITH INTERMITTENT EXPOSURES IN MAN SHOW THAT MORE THAN ORDINARY CARE IS NEEDED TO AVOID SKIN CONTACT & INHALATION.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
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Environmental Concentrations
4-Vinylpyridine was detected in cigarette smoke at an unspecified concentration(1).
Pollution Sources
4-Vinylpyridine's production and use as a monomer for polyvinylpyridine polymers and in synthetic rubbers, photographic film, ion exchange resins as well as pharmaceuticals(1) may result in its release to the environment through various waste streams(SRC).
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a water solubility of 29,100 mg/l at 25 °C(2) and a regression-derived equation(3), indicates that 4-vinylpyridine is expected to have very high mobility in soil(SRC). 4-Vinylpyridine has a pKa of 5.62(7), which indicates that this compound will partially exist in the protonated form in moist acidic soils, and cations adsorb more strongly to soils than neutral molecules. Therefore, the mobility of 4-vinylpyridine is expected to be much lower in acidic soils than in neutral or alkaline soil(SRC). Volatilization of the neutral species of 4-vinylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.2X10-6 atm-cu m/mole(SRC), using a group contribution estimation method(4). However, the protonated form will not volatilize(SRC). The potential for volatilization of 4-vinylpyridine from dry soil surfaces may exist(SRC) based upon an extrapolated vapor pressure of 1.7 mm Hg(5). Biodegradation of 4-vinylpyridine in soil is not expected to be a major fate process based on a single aerobic screening test showing that this compound was not biodegraded over a 4-week period(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a water solubility of 29,100 mg/l at 25 °C(2) and a regression-derived equation(3), indicates that 4-vinylpyridine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.2X10-6 atm-cu m/mole(SRC), developed using a group contribution estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 12 and 90 days, respectively(SRC). The pKa of 4-vinylpyridine is 5.62(7), indicating this compound will partially exist in the ionized form in acidic waters and cations do not volatilize(SRC). According to a classification scheme(5), BCF values of 48 to 96 measured in carp(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation of 4-vinylpyridine in water is not expected to be a major fate process based on a single aerobic screening test showing that this compound was not biodegraded over a 4-week period(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-vinylpyridine, which has an extrapolated vapor pressure of 1.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-vinylpyridine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14 hours(SRC), calculated from its estimated rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Vapor-phase 4-vinylpyridine is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 13 hours(SRC), calculated from its rate constant of 2.1X10-17 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3).
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Abiotic Degradation
The rate constant for the vapor-phase reaction of 4-vinylpyridine with photochemically-produced hydroxyl radicals has been estimated as 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 4-vinylpyridine with ozone has been estimated as 2.1X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). 4-Vinylpyridine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Data are not available to assess this compound's potential for direct photolysis. A pKa of 5.62(4) indicates 4-vinylpyridine will partially exist in the protonated form in acidic waters and soils.
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Bioconcentration
72.44|BCF values of 48 to 96 were measured in carp at concentrations of 2 and 20 ug/l during an 8-week study(1). According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is moderate(SRC).
Mobility
15.14 L/kg|The Koc of 4-vinylpyridine is estimated as 15(SRC), using a measured water solubility of 29,100 mg/l at 25 °C(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-vinylpyridine is expected to have very high mobility in soil. The pKa of 4-vinylpyridine is 5.62(4), which indicates that this compound will partially exist in the protonated form under acidic conditions. Cations adsorb more strongly to soil surfaces than neutral molecules thus adsorption of 4-vinylpyridine is expected to be greater in acidic soils(SRC).
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Volatilization
The Henry's Law constant for 4-vinylpyridine is estimated as 3.2X10-6 atm-cu m/mole(SRC) using a group contribution estimation method(1). This Henry's Law constant indicates that 4-vinylpyridine is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 12 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 90 days(SRC). 4-Vinylpyridine's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). However, 4-vinylpyridine is a weak base with a pKa of 5.62(3), which indicates this compound will partially exist in the protonated form in acidic conditions; cations do not volatilize from either moist soil or water surfaces. The potential for volatilization of 4-vinylpyridine from dry soil surfaces may exist(SRC) based upon an extrapolated vapor pressure of 1.7 mm Hg(4).
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Human Exposure
The most probable human exposure to 4-vinylpyridine would be occupational exposure, which may occur through dermal contact or inhalation at places where it is produced or used. NIOSH (NOES Survey 1981-1983) has statistically estimated that 3 workers are potentially exposed to 4-vinylpyridine in the USA(1). Non-occupational exposures are likely to occur from the passive and active inhalation of cigarette smoke(2).
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Mesh
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)
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Absorption
... /IT IS/ ABSORBED FROM GI TRACT, SKIN & RESP TRACT IN ... /RATS & MICE/.|MAJORITY OF /PYRIDINE/ DERIVATIVES TESTED ... PENETRATE INTACT GUINEA PIG SKIN READILY. AMINOPYRIDINES, VINYLPYRIDINES & 4-PICOLINE PENETRATE SKIN MOST RAPIDLY & AMYL DERIV & 5-ETHYL-2-METHYLPYRIDINE ARE LEAST READILY ABSORBED. /VINYLPYRIDINES/|PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION ... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/
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Antidote
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/
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Human Toxicity Excerpts
BRIEF EXPOSURES TO UNDETERMINED CONCN OF ... 4-VINYLPYRIDINE DURING LAB USE ... CAUSED EYE, NOSE & THROAT IRRITATION ... HEADACHE, NAUSEA, NERVOUSNESS, & ANOREXIA. SYSTEMIC SYMPTOMS ARE MILD & TRANSIENT RESEMBLING THOSE OBSERVED WITH PYRIDINE EXPOSURE ... APPARENTLY PRODUCED BY LOWER CONCN.|DIRECT SKIN CONTACT WITH THE LIQUID RESULTS IN BURNING PAIN, FOLLOWED BY FAIRLY SEVERE SKIN BURNS IN SPITE OF IMMEDIATE ATTEMPTS TO CLEANSE THE SKIN. BURNS DEVELOP REDDISH BROWN COLOR THAT DISAPPEARS IN ... ABOUT 1 MO. SKIN SENSITIZATION HAS BEEN OBSERVED ... .|INHALATION TOXICITY OF 4-VINYLPYRIDINE IS GREATER THAN ... 2-VINYLPYRIDINE, & 4-VINYLPYRIDINE IS DEFINITELY MORE IRRITATING TO MUCOUS MEMBRANES.|SEVERAL CASES OF TRANSIENT MUCOUS MEMBRANE IRRITATION, SYSTEMIC SYMPTOMS, SKIN BURNS & SKIN SENSITIZATION ... HAVE BEEN OBSERVED DURING MFR & IN LABORATORY PILOT-PLANT USE.
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Mesh Entry Terms
4-ethenylpyridine
Production
Although 4-vinylpyridine has been used for various purposes, its total annual demand is presumed to be only several hundred tons.
Manufacturing Info
All other basic organic chemical manufacturing|Pyridine, 4-ethenyl-: ACTIVE|Commercial ... 4-vinylpyridine ... supplied with small amt of polymerization inhibitors added.|... been investigated for use in synthetic rubbers, photographic film, ion exchange resins, and other polymers as well as pharmaceuticals.
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4-Vinylpyridine
Henan Tianfu Chemical Co.,Ltd
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4-Vinylpyridine
Hangzhou KieRay Chem Co., Ltd.
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4-Vinylpyridine
Hangzhou Tianye chemicals Co., Ltd
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4-Vinylpyridine
Dayang Chem (Hangzhou) Co., Ltd.
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4-Vinylpyridine
Finetech Industry limited.
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Tel: Update Time:2018/11/21
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12. Related Questions
How is 4-Vinylpyridine Produced?4-Vinylpyridine is an important chemical product. The production process of 4-Vinylpyridine involves the synthesis of 4-hydroxyethylpyridine by adding a quantitative amount of 4-methylpyridine and pol..
What are the applications of 4-Vinylpyridine?4-Vinylpyridine, also known as 4-Vinylpyridine, is a colorless or light yellow liquid at room temperature and pressure. It has a distinct irritating odor and is soluble in water to a certain extent, a..
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