4-Vinylpyridine
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4-Vinylpyridine
structure -
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CAS No:
100-43-6
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Formula:
C7H7N
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Chemical Name:
4-Vinylpyridine
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Synonyms:
Pyridine,4-ethenyl-;Pyridine,4-vinyl-;4-Ethenylpyridine;4-Vinylpyridine;γ-Vinylpyridine;NSC 18256;2-(4-Pyridyl)ethylene;80347-34-8
- Categories:
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CAS No:
4-Vinylpyridine Basic Attributes
105.14
105.14
104506
202-852-0
I56G67XM8D
18256
DTXSID0051499
RED TO DARK BROWN LIQUID
29333990
Characteristics
12.9
1.21
Clear colorless to yellow-brown Liquid
0.9800 g/cm3 @ Temp: 20 °C
<25 °C
65 °C @ Press: 15 Torr
125 °F
n20/D 1.549(lit.)
H2O: 29 G/L (20 ºC)
-20°C
1.71 mm Hg @ 25 deg C
Oral-rat LD50: 100 mg/kg; Oral-Mouse LD50: 161 mg/kg
Open flame is flammable; heated to decompose toxic nitrogen oxide gas
Pungent unpleasant odor
pKa= 5.62 (conjugate acid)
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/
Safety Information
II
6.1
UN 3073 6.1/PG 2
3
10-25-34-42/43-23/25
23-26-36/37/39-45-28A-16
UU1045000
T
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable. Incompatible with strong acids, strong oxidizing agents.
P280-P301 + P310 + P330-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338-P333 + P313
H226-H301-H314-H317
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.
|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P284, P285, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P320, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 182 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 95 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501
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/
Fire hazard is moderate ... .
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.
/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/|For more DOT Emergency Guidelines (Complete) data for 4-VINYLPYRIDINE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
BRIEF EXPOSURES TO UNDETERMINED CONCN OF ... 4-VINYLPYRIDINE DURING LAB USE ... CAUSED EYE, NOSE & THROAT IRRITATION ... .
4-Vinylpyridine was detected in cigarette smoke at an unspecified concentration(1).
Toxicity
highly toxic
LD50 RAT ORAL 100-200 MG/KG|LD50 RAT INTRAPERITONEAL 50 MG/KG|LD50 MICE ORAL 200-400 MG/KG|LD50 MICE INTRAPERITONEAL 100-200 MG/KG|For more Non-Human Toxicity Values (Complete) data for 4-VINYLPYRIDINE (8 total), please visit the HSDB record page.
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).
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).
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.
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).
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).
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).
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).
Drug Information
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.)
... /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/
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/
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.
4-ethenylpyridine
4-Vinylpyridine Use and 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.
Synthetic styrene-butadiene latex is also used in medicines such as Kesiping and Betadine hydrochloride. It is also the raw material of ion exchange resin. It produces weakly basic ion exchange resin and ion exchange membrane to separate heavy metal ions; high molecular polymer modifier (benzene is added to polyvinyl chloride and polyvinyl acetate to improve polymer Mechanical strength and flexural strength); The polymer made by graft copolymerization of this product with a linear polymer is a cationic surfactant.
Intermediates
Although 4-vinylpyridine has been used for various purposes, its total annual demand is presumed to be only several hundred tons.
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.
CONCN CAN BE DETERMINED IN AIR BY COLLECTION IN DISTILLED WATER & MEASUREMENT OF ... UV ABSORPTION SPECTRUM.|NIOSH Method 1613. Analysis of air samples for pyridine using gas chromatography with FID detection. Working range of 1 to 14 ppm (3 to 45 mg/cu m) for a 100-L air sample. /Pyridine/|Pyridine and its derivatives in water and sediment were determined by gas chromatography. Recovery was 95, 90, and 84% from purified water, river water, and sediment, respectively. The detection limit was 0.001 mg/l water and 0.01 mg/l sediment. /Pyridine and its derivatives/|VARIOUS TLC SYSTEMS FOR THE SEPARATION OF 2-, 3-, & 4-SUBSTITUTED PYRIDINES ARE DESCRIBED.
Computed Properties
Molecular Weight:105.14
XLogP3:1.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:105.057849228
Monoisotopic Mass:105.057849228
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:72.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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