Grundinformationen
- Standard-SMILES
C=Cc1ccc(C)nc1- InChIKey
VJOWMORERYNYON-UHFFFAOYSA-N- Summenformel
- C8H9N
- Durchschnittliche Molmasse
- 119,16 g/mol
- Monoisotopische Masse
- 119,07349929
Überblick
Pyridine, 2-methyl-5-vinyl- is a clear to faintly opalescent liquid. Used as a monomer for resins, as an oil additive, ore flotation agent; and dye acceptor. (EPA, 1998)
Namen und Bezeichner
- Bevorzugter Name
- 2-Methyl-5-vinylpyridine
- IUPAC
- 5-ethenyl-2-methylpyridine
- Lokaler Name
- 5-Ethenyl-2-methylpyridin
- Englischer Name
- 2-Methyl-5-vinylpyridine
- Summenformel
- C8H9N
- Molmasse
- 119.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
140-76-1、25038-86-2- PubChem CID
- 8817
- DTXSID
DTXSID2059699- UNII
- 34ET764YF8
- EC Number
- 205-432-5
- Nikkaji
- J38.338D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2
- Polarare Oberfläche (TPSA)
- 12,9 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 98,7
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Nitrogen Compounds -> Pyridines
Flammable agents - 2nd degree
Density
0.978 to 0.982 at 68 °F (EPA, 1998)
0.978-0.982 @ 20 °C/20 °C
0.98 @ 20°C
Flash Point
165 °F (EPA, 1998)
73.9 °C (Open cup)
Boiling Point
358 °F at 760 mmHg (EPA, 1998)
181 °C
181 °C @760 [mm Hg]
Vapor Pressure
1.18 [mmHg]
1.18 mm Hg @ 25 °C
1.7 [mm Hg] @25 °C
Physical Description
Pyridine, 2-methyl-5-vinyl- is a clear to faintly opalescent liquid. Used as a monomer for resins, as an oil additive, ore flotation agent; and dye acceptor. (EPA, 1998)
Clear to slightly opalescent liquid; [HSDB]
Physikochemische Eigenschaften
- Schmelzpunkt
- -12 °C · -12.0 °C
- Siedepunkt
- 212.46 °C · 212.46°C (rough estimate)
- Dichte
- 1 · 1.0000 (rough estimate)
- Brechungsindex
- 1.533 · 1.5330 (estimate)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 5.58 · 5.58±0.10(Predicted)
- Henry's Law Constant
- 2.2 · 2.2×100 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- InChI=1S/C8H9N/c1-3-8-5-4-7(2)9-6-8/h3-6H,1H2,2H3
- InChIKey
- VJOWMORERYNYON-UHFFFAOYSA-N
- SMILES
- C1(C)=NC=C(C=C)C=C1
- CAS Datenbank
- 140 · 140-76-1(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-Methyl-5-vinylpyridine(140-76-1)
- EPA chemische Informationen
- 2 · 2-Methyl-5-vinylpyridine (140-76-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H226 (12.5%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P320, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 16 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Fire Hazards
When heated to decomposition, it emits toxic fumes of nitrogen oxides. (Non-Specific -- Combustible Liquid, n.o.s.) Flammable/combustible material; may be ignited by heat, sparks, or flames. Vapors may travel to a source of ignition and flash back. Container may explode in heat of fire. (EPA, 1998)
Reactivity Profile
PYRIDINE, 2-METHYL-5-VINYL- neutralizes acids in exothermic reactions to form salts plus water. Can polymerize exothermically. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
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/
For more DOT Emergency Guidelines (Complete) data for PYRIDINE, 2-METHYL-5-VINYL (8 total), please visit the HSDB record page.
NFPA Hazard Classification
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
0 - Materials that in themselves are normally stable, even under fire conditions.
Sicherheit und Schutzausrüstung
Fire Fighting
(Non-Specific -- Combustible Liquid, n.o.s.) Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire. Move container from fire area if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. For massive fire in cargo area, use unmanned hose holder or monitor nozzles; if this is impossible, withdraw from area and let fire burn. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire.
Nonfire Spill Response
(Non-Specific -- Combustible Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Shut off ignition sources; no flares, smoking, or flames in hazard area. Stop leak if you can do so without risk. Use water spray to reduce vapors. Absorb spills with sand or noncombustible absorbent material. For large spills dike far ahead. (EPA, 1998)
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
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.
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.
Protective Action Criteria (PAC)
0.17 [mg/m3]
1.9 [mg/m3]
6.6 [mg/m3]
Personal Protective Equipment (PPE)
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
Vapor concentration: 250 ppm or less; a chemical cartridge respirator with a full facepiece and an organic vapor cartridge(s), a gas mask with a chin-style or a front- or back-mounted organic vapor canister, any supplied-air respirator with a full facepiece, helmet, or hood, or any self-contained breathing apparatus with a full facepiece. 3600 ppm or less: a Type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure mode or with a full facepiece, helmet, or hood operated in continuous-flow mode. Greater than 3600 ppm or entry and escape from unknown concentrations: self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode. /Pyridine/
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/
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that 2-methyl-5-vinylpyridine is expected to have moderate mobility in soil(SRC). 2-Methyl-5-vinylpyridine has a pKa of 5.67(5), 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 2-methyl-5-vinylpyridine is expected to be much lower in acidic soils than in neutral or alkaline soil(SRC). Volatilization of the neutral species of 2-methyl-5-vinylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, the protonated form will not volatilize(SRC). The potential for volatilization of 2-methyl-5-vinylpyridine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1.18 mm Hg(4). Biodegradation data were not located for 2-methyl-5-vinylpyridine; however a structurally-similar compound, 2-methyl-5-ethylpyridine was not biodegraded during a 28-day chemostat experiment(6) indicating that this compound may also be resistant to biodegradation in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that 2-methyl-5-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 4.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant 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 9 and 71 days, respectively(SRC). The pKa of 2-methyl-5-vinylpyridine is 5.67(8), 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), an estimated BCF of 11(SRC), from an estimated log Kow of 2.25(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not located for 2-methyl-5-vinylpyridine; however a structurally-similar compound, 2-methyl-5-ethylpyridine, was not biodegraded during a 28-day chemostat experiment(9) indicating that this compound may also be resistant to biodegradation in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methyl-5-vinylpyridine, which has a vapor pressure of 1.18 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 2-methyl-5-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 rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Vapor-phase 2-methyl-5-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).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-methyl-5-vinylpyridine can be estimated to be 170(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methyl-5-vinylpyridine is expected to have moderate mobility in soil. The pKa of 2-methyl-5-vinylpyridine is 5.67(3), 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 2-methyl-5-vinylpyridine is expected to be greater in acidic soils(SRC).
Environmental Biodegradation
AEROBIC: No data were located for 2-methyl-5-vinylpyridine although a chemostat experiment for a structurally-similar compound suggests that 2-methyl-5-vinylpyridine may be resistant to biodegradation. 2-Methyl-5-ethylpyridine was not biodegraded over a 28-day chemostate experiment using groundwater; 2-methyl-5-ethylpyridine was present initially at 5276 ug/l with a dilution rate of 0.067 per day)(1). The effluent concentration was 5075 ug/l(1). biodegradation, as measured by BOD, were reported for 2-vinyl- and 4-vinylpyridine (initially present at 100 mg/l) in the 4-week Japanese MITI test(1).
Environmental Bioconcentration
An estimated BCF of 11 was calculated for 2-methyl-5-vinylpyridine(SRC), using an estimated log Kow of 2.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for 2-methyl-5-vinylpyridine is estimated as 4.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-methyl-5-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 9 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 71 days(SRC). 2-Methyl-5-vinylpyridine's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). However, 2-methyl-5-vinylpyridine is a weak base with a pKa of 5.67(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 2-methyl-5-vinylpyridine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1.18 mm Hg(4).
Non-Human Toxicity Excerpts
2-Methyl-5-vinylpyridine was admin at 157 mg/kg orally daily to rats throughout pregnancy. The structure and composition of the liver and the structure and growth pattern of the skin were disrupted in the offspring of the treated rats, indicating placental permeability to these pyridine derivatives or their toxic by-products.
Chronic intoxication changes in rats caused by 2-methyl-5-vinylpyridine were related to the histohematic barrier. These included changes in structural elements of the blood-brain barrier of the brain vessels, endothelium and epithelium of the vascular plexus, and Kupffer cells, in the content and distribution of nucleotides, proteins, and enzymes, in organ function, etc.
Daily admin of 0.1 or 1 mg 2-methyl-5-vinylpyridine/kg for 30-180 days injured neurons of the sensory and motor sections of the spinal cord of rats. Chromatolysis and vacuolization of neurons occurred in the horns of the spinal cord. The number of neurons with low levels of succinate dehydrogenase and glutamate dehydrogenase activity was incr.
Daily oral admin of 300 mg 2-methyl-5-vinylpyridine for 10 days decr the number of highly active cells in the /hypothalamic-hypophyseal neurosecretory system (HHNS)/ of rats, decr the number of less active cells, decr the diameter of cell nuclei, and induced the accumulation of neurosecretion in the nerve fibers and neurohypophysis. Initially the formation of neurosecretion and its translocation into the blood stream was disturbed, and later the formation was disturbed in the hypothalamus. The overall function of the /hypothalamic-hypophyseal neurosecretory system/ was inhibited and the secretion of neurohormones into the blood stream was disturbed.
For more Non-Human Toxicity Excerpts (Complete) data for PYRIDINE, 2-METHYL-5-VINYL (6 total), please visit the HSDB record page.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 2-methyl-5-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 2-methyl-5-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). 2-Methyl-5-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 5.67(4) indicates 2-methyl-5-vinylpyridine will partially exist in the protonated form in acidic waters and soils.
Environmental Fate/Exposure Summary
2-Methyl-5-vinylpyridine's production and use as a monomer for resins, oil additive, ore flotation agent and dye acceptor may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 1.18 mm Hg at 25 °C indicates 2-methyl-5-vinylpyridine will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methyl-5-vinylpyridine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone; the half-lives for these reactions in air are estimated to be 14 and 13 hours, respectively. If released to soil, 2-methyl-5-vinylpyridine is expected to have moderate mobility based upon an estimated Koc of 170. 2-Methyl-5-vinylpyridine has a pKa of 5.67, which indicates that this compound will partially exist in the protonated form in moist acidic soils; cations adsorb more strongly to soils than neutral molecules. Therefore, the mobility of 2-methyl-5-vinylpyridine is expected to be much lower in acidic soils than in neutral or alkaline soils. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 4.4X10-6 atm-cu m/mole. However, in moist acidic soils, where the protonated form is the dominant species, volatilization will not be important because cations do not volatilize. 2-Methyl-5-vinylpyridine may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not located for 2-methyl-5-vinylpyridine; however a structurally-similar compound, 2-methyl-5-ethylpyridine, was not biodegraded during a 28-day chemostat experiment indicating that this compound may also be resistant to biodegradation in the environment. Volatilization of the neutral species from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 9 and 71 days, respectively. In acidic waters where the protonated form is the dominant species, volatilization will not be an important fate process since cations do not volatilize. An estimated BCF of 11 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to 2-methyl-5-vinylpyridine may occur through inhalation and dermal contact with this compound at workplaces where 2-methyl-5-vinylpyridine is produced or used. (SRC)
Regulatorische Informationen
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Pyridine, 2-methyl-5-vinyl is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Sicherheitsdaten
- tsca
- TSCA listed
- ridadr
- 2810
- hs_code
- 2933499090
- Toxizität
- LD50 oral in rat: 1300uL/kg
- hazard_class
- 6.1(b)
- packing_group
- III
- Giftige Stoffe Daten
- 140-76-1(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Absorption, Distribution and Excretion
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/
Verwendung und Herstellung
Uses
Used as monomer for resins, oil additive, ore flotation agent, dye acceptor, and flocculating agent; [HSDB]
Metal Extraction and Refining [Category: Industry]
Monomer for resins; oil additive; ore flotation agent; dye acceptor
As a decolorizing ion exchange resin.
As a flocculating agent.
General Manufacturing Information
Pyridine, 5-ethenyl-2-methyl-: ACTIVE
The polymer of 2-methyl-5-vinylpyridine was formerly used as a coating material for medicine tablets; today, it is not used at all.
Anwendungen
VerwendenMonomer for resins, oil additive, ore flotationagent, dye acceptor.
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