HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Vinylpyridine
4VP · 4-Ethenylpyridine · Pyridine,4-ethenyl- · 4-vinylpyridine monomer · 4-VINYLPYRIDINE · 4-vinyl-pyridin · Vinylpyridine,4- · 4-ethenyl-pyridin
Identifiers & Physical Properties
| CAS No. | 100-43-6 |
|---|---|
| Molecular formula | C7H7N |
| Average molar mass | 105.14 g/mol |
| Monoisotopic mass | 105.05784923 g/mol |
| SMILES | C=Cc1ccncc1 |
| InChIKey | KFDVPJUYSDEJTH-UHFFFAOYSA-N |
| PubChem CID | 7502 |
| ChEMBL | CHEMBL4550330 |
| EC No. | 202-852-0 |
| DTXSID | DTXSID0051499 |
Chemical & Physical Properties
| XLogP | 1.6 |
|---|---|
| Topological polar surface area | 12.9 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 72 |
| Odor | Pungent unpleasant odor |
| Density | 0.9800 @ 20 °C/4 °C0.975 g/mL at 25 °C (lit.) |
| Color/Form | RED TO DARK BROWN LIQUID |
| Solubility | Soluble in alcohol and chloroformslightly soluble in etherIn water, 29,100 mg/l @ 20 °CChloroform, Methanol (Slightly)29 G/L (20 ºC) |
| Boiling point | 65 °C @ 15 mm Hg62-65 °C/15 mmHg (lit.) |
| Decomposition | DECOMPOSITION BY HEAT IS ACCOMPANIED BY RELEASE OF DANGEROUS CYANIDE FUMES.When heated to decomp ... emits toxic fumes of /nitrogen oxides/. |
| 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.... ACCLIMATIZED INDIVIDUALS CAN READILY LEARN TO TOLERATE CONCN THAT WILL CAUSE ACUTE SYMPTOMS & IRRITATION. ... OLFACTORY FATIGUE OCCURS QUICKLY.1.16 mg/cu m (odor low)1.94 mg/cu m (odor high). |
| Vapor pressure | 1.71 [mmHg]VP: 2 mm Hg @ 25 °C1.71 mm Hg @ 25 °C2.28hPa at 25℃ |
| Refractive index | INDEX OF REFRACTION: 1.5449 @ 20 °C/DMAX ABSORPTION (ALC): 242.5 NM (LOG E= 4.12)SADTLER REF NUMBER: 1249 (IR, PRISM)n20/D 1.549(lit.) |
| Physical Description | LiquidRed to dark-brown liquid[HSDB] |
| Dissociation Constants | pKa= 5.62 (conjugate acid) |
| Kovats Retention Index | 1026 |
| Melting point | <25 °C |
| Flash point | 125 °F |
| Storage conditions | -20°C |
| Physical state | Liquid |
| pKa (acidity coefficient) | pK1:5.62(+1) (25°C) |
| Color | Clear colorless to yellow-brown |
| BRN | 104506 |
| Henry's law constant | 1.2×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| InChI | 1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2 |
| InChIKey | KFDVPJUYSDEJTH-UHFFFAOYSA-N |
| SMILES | C=Cc1ccncc1 |
| LogP (partition coefficient) | 1.36 at 20℃ |
| CAS DataBase Reference | 100-43-6(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | I56G67XM8D |
| NIST Chemistry Reference | Pyridine, 4-ethenyl-(100-43-6) |
| EPA Substance Registry System | 4-Vinylpyridine (100-43-6) |
| UNSPSC Code | 12162002 |
| NACRES | NA.23 |
| GHS pictogram | GHS02,GHS05,GHS06,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H330-H301-H314-H317-H335-H410-H226 |
| GHS precautionary statements | P501-P273-P272-P260-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P391-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | T |
| Risk statements (R) | 10-25-34-42/43-23/25 |
| Safety statements (S) | 23-26-36/37/39-45-28A-16 |
| UN transport number | UN 3073 6.1/PG 2 |
| Water hazard class (WGK) | 3 |
| RTECS number | UU1045000 |
| F | 8-10 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Flam. Liq. 3Skin Corr. 1BSkin Sens. 1 |
| Packing group | II |
| Customs code | 29333990 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 100-43-6(Hazardous Substances Data) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 16.6% (37 of 223) of reports.DangerH226 (83.4%): Flammable liquid and vapor [Warning Flammable liquids]H301 (78%): Toxic if swallowed [Danger Acute toxicity, oral]H311 (52%): Toxic in contact with skin [Danger Acute toxicity, dermal]H314 (75.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H317 (83%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (50.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H330 (13%): Fatal if inhaled [Danger Acute toxicity, inhalation]H331 (50.2%): Toxic if inhaled [Danger Acute toxicity, inhalation]H411 (57.8%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 223 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 37 of 223 reports by companies.There are 14 notifications provided by 186 of 223 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Pyridine, 4-ethenyl-Pyridine, 4-ethenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridine, 4-ethenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 24-04-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/101264-Vinylpyridine: Does not have an individual approval but may be used under an appropriate group standard |
| Fire potential | Fire hazard is moderate ... . |
| Hazards summary | Irritating to eyes, nose, and throatCauses skin burns and skin sensitization[HSDB] May cause pneumonitis and pulmonary edema after inhalation of high concentrations[MSDSonline] Can cause contact urticaria (nonimmunological) and allergic contact dermatitis[Kanerva, p. 1845] See Pyridine. |
| DOT Emergency Guidelines | /GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXICmay 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, inhibitedVinylpyridines, 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/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/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 ONLYit is not effective in spill situations where direct contact with the substance is possible. /Vinylpyridines, inhibitedFor more DOT Emergency Guidelines (Complete) data for 4-VINYLPYRIDINE (8 total), please visit the HSDB record page. |
| Hazard Classes and Categories | Flam. Liq. 3 (83.4%)Acute Tox. 3 (78%)Acute Tox. 3 (52%)Skin Corr. 1B (75.3%)Skin Sens. 1 (83%)Eye Dam. 1 (50.7%)Acute Tox. 2 (13%)Acute Tox. 3 (50.2%)Aquatic Chronic 2 (57.8%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%)Flammable liquids - Category 3Acute toxicity (Oral) - Category 3Acute toxicity (Inhalation: Vapours) - Category 1Skin corrosion/irritation - Category 2Serious eye damage/eye irritation - Category 2ASkin sensitization - Category 1Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)Hazardous to the aquatic environment (Acute) - Category 1Hazardous to the aquatic environment (Long-term) - Category 1 |
| Shipment Methods and Regulations | 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. |
| Shipping Name/ Number DOT/UN/NA/IMO | UN 3073Vinylpyridines, inhibitedIMO 6.1 |
| Skin, Eye, and Respiratory Irritations | BRIEF EXPOSURES TO UNDETERMINED CONCN OF ... 4-VINYLPYRIDINE DURING LAB USE ... CAUSED EYE, NOSE & THROAT IRRITATION ... . |
| 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. |
| Preventive Measures | ALL OPERATIONS INVOLVING HANDLING...SHOULD BE CONDUCTED IN WELL-VENTILATED CONDITIONSPROCESS 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. |
| Personal Protective Equipment (PPE) | 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/ |
| 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). |
| Adverse effects | Dermatotoxin - Skin burns.Skin Sensitizer - An agent that can induce an allergic reaction in the skin.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| Soil Adsorption/Mobility | 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). |
| 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. |
| Artificial 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 Biodegradation | AEROBIC: 4-Vinylpyridine, present at 100 mg/l, was not biodegraded, as measured by BOD, in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/Soil | 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 conditionscations 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). |
| Non-Human Toxicity Excerpts | ... 4-VINYLPYRIDINE /IS/ ... BETWEEN THE AMINOPYRIDINES & PYRIDINE IN ... ACUTE TOXICITY FOR RATS & MICE ... /IT IS/ ABSORBED FROM GI TRACT, SKIN & RESP TRACT IN THESE ANIMALS. ABSORPTION BY THESE ROUTES RESULTS IN WEAKNESS, ATAXIA, VASODILATATION, RESP DISTRESS, & CONVULSIONS.2.0 HR WERE REQUIRED FOR 100% MORTALITY TO OCCUR IN RATS INHALING A CALCULATED CONCN OF 2000 PPM. /FROM TABLE/MORTALITY RATE WAS 0/3 FOR RATS EXPOSED BY INHALATION TO 150 PPM FOR 6 HR. /FROM TABLE/... EXPOSURE TO VAPOR ... RESULTS IN NASAL & EYE IRRITATION WITH ACCELERATED RESPIRATION & RESPIRATORY DISTRESS /IN RATS & MICE/. INSTILLATION OF UNDILUTED /LIQUID/ ... IN RABBIT EYE CAUSES MODERATELY SEVERE EYE IRRITATION. SKIN SENSITIZATION WAS PRODUCED IN SOME GUINEA PIGS ... .For more Non-Human Toxicity Excerpts (Complete) data for 4-VINYLPYRIDINE (6 total), please visit the HSDB record page. |
| Environmental 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. |
| Probable Routes of 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). |
| Other Environmental Concentrations | 4-Vinylpyridine was detected in cigarette smoke at an unspecified concentration(1). |
| F | 8-10 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | UU1045000 |
| UN transport number | UN 3073 6.1/PG 2 |
| Customs code | 29333990 |
| Risk statements (R) | 10-25-34-42/43-23/25 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS06,GHS09 |
| Hazard symbols | T |
| Safety statements (S) | 23-26-36/37/39-45-28A-16 |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Flam. Liq. 3Skin Corr. 1BSkin Sens. 1 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H330-H301-H314-H317-H335-H410-H226 |
| REACH registrations | Active |
| GHS precautionary statements | P501-P273-P272-P260-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P391-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405 |
| Hazardous substances data | 100-43-6(Hazardous Substances Data) |
Applications & Uses
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].
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.
Preparation & Synthesis
Preparation
4-Vinylpyridine is synthesized by reacting 4-picoline with formaldehyde to generate 4-pyridineethanol, which is then dehydrated.