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2-ethenylpyridine

CAS number:27476-03-5    molecular formula:C7H7N

overview

compound introduction

另见:乙烯基吡啶,稳定(注释已移至)。

Specs

Chinese alias2-丁吡
English alias-
CAS number27476-03-5molecular formulaC7H7N
molecular weight105.14Exact mass-
PSA12.9logp1.5

numbering system

CAS27476-03-5
UNIIDT4UV4NNKX
HMDB IDHMDB0245325
WikidataQ4596922
ChEMBL IDCHEMBL2134875
UN Number3073
Wikipedia2-Vinylpyridine
NSC NumberNSC Number: NSC18255
AIDS Number159874
ICSC Number1232
PubChem CID7521
Related CAS100-69-6(FREE BASE)
Nikkaji NumberJ38.336H
DSSTox Substance IDDTXSID1026667
European Community (EC) Number202-879-8
PubChem Reference Collection SID500732943

physicochemical properties

LogP1.39
OdorPungent unpleasant odor
XLogP31.5
DensityRelative density (water = 1): 1.00
Viscosity1.17 mPa.s @ 20 °C
Color/FormCOLORLESS LIQUID
Complexity78.5
Exact Mass105.057849228
SolubilitySolubility in water: moderate
Flash Point42 °C
Boiling Point159-160 °C
DecompositionWhen heated to decomp ... emits toxic fumes of /nitrogen oxides/.
Formal Charge0
Odor Threshold1.16 mg/cu m (odor low); 1.94 mg/cu m (odor high).
Vapor PressureVapor pressure, kPa at 44.5 °C: 1.33
Chemical ClassesNitrogen Compounds -> Pyridines
Heavy Atom Count8
Molecular Weight105.14
Refractive IndexMAX ABSORPTION (ALCOHOL): 238 NM (LOG E= 4.1); 282 NM (LOG E= 3.8); INDEX OF REFRACTION: 1.5495 AT 20 °C/D; SADTLER REFERENCE NUMBER: 15806 (IR, PRISM); 155 (NMR, VARIAN)
Monoisotopic Mass105.057849228
Isotope Atom Count0
Physical DescriptionCOLOURLESS LIQUID WITH PUNGENT ODOUR.
Rotatable Bond Count1
Dissociation Constantsiupacpka
Kovats Retention IndexSemi-standard non-polar: 932
Hydrogen Bond Donor Count0
Covalently-Bonded Unit Count1
Hydrogen Bond Acceptor Count1
Other Experimental PropertiesDissolves 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/
Topological Polar Surface Area12.9 Ų
Defined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Atom Stereocenter Count0
Undefined Bond Stereocenter Count0

Safety information

Fire Hazards:
Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 32 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion. See Chemical Dangers.
Safe Storage:
Fireproof. Separated from strong oxidants, strong acids and food and feedstuffs. Keep in the dark. Well closed. Store only if stabilized.
Fire Fighting:
Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
Toxicity Data:
LC50 (rat) = 610 mg/m3
Eye Prevention:
Wear face shield or eye protection in combination with breathing protection.
Fire Potential:
FIRE HAZARD IS MODERATE.
Adverse Effects:
Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Exposure Routes:
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
Fire Prevention:
NO open flames, NO sparks and NO smoking. Above 32 °C use a closed system, ventilation and explosion-proof electrical equipment. Do NOT expose to friction or shock.
Hazards Summary:
A skin, eye, nose, and mucous membrane irritant; May cause skin burns and sensitization; Emergency treatment: Pyridine; Pyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppm; It can cause liver and kidney injury; May cause delayed burns to skin; A severe eye and respiratory tract irritant; May cause skin sensitization; [ICSC] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May be absorbed through skin; [Alfa Aesar MSDS] May cause burns; Toxic if swallowed; Harmful if inhaled; May cause allergic skin reactions; [Aldrich MSDS] Vinylpyridines, stabilized (UN3073) has warning of explosive polymerization; [ERG 2016] See Pyridine.
Inhalation Risk:
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin Prevention:
Protective gloves. Protective clothing.
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.
Spillage Disposal:
Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit.
UN Classification:
UN Hazard Class: 6.1; UN Subsidiary Risks: 3 and 8; UN Pack Group: II
Environmental Fate:
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-vinylpyridine, which has an estimated vapor pressure of 2.6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-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 6.8 hours(SRC), calculated from its rate constant of 5.67X10-11 cu cm/molecule-sec at 25 °C(3). Vapor-phase 2-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...
First Aid Measures:
Ingestion First Aid: Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
Signs and Symptoms:
Ingestion Exposure: Further see Inhalation.
Exposure Prevention:
PREVENT GENERATION OF MISTS! AVOID ALL CONTACT!
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.
Ingestion Prevention:
Do not eat, drink, or smoke during work.
Inhalation Prevention:
Use ventilation, local exhaust or breathing protection.
TSCA Test Submissions:
UNREVIEWED | 2-Vinylpyridine (CAS # 100-60-6, 97.34%) was evaluated for subchronic oral toxicity in Crl:CD rats (30/sex/dose level) gavaged with doses of 0, 20, 60, or 180 mg/kg/day, 5 days/week for approximately 43 or 92 days. Three female rats (2/30 at 180 mg/kg/day, 1/30 at 60 mg/kg/day) died of a potential toxic cause on Days 15, 65, and 42, respectively. High dose rats exhibited clinical signs including convulsions and sialorrhea. A high dose regimen was also associated with diminished weight gain with decreased feed consumption in males, reduced feed consumption in 92-day females, slight platelet count elevations (males and females), and slightly depressed aspartate aminotransferase activity in males. On necropsy, "relevent lesions" in the study lethalities included pulmonary cong...
Regulatory Information:
New Zealand EPA Inventory of Chemical Status: 2-Vinylpyridine (stabilized with 4-t-butylpyrocatechol): Does not have an individual approval but may be used under an appropriate group standard
Effluent Concentrations:
2-Vinylpyridine was detected in 2 of 21 industrial categories of wastewater effluents(1). Extract from the wastewater of a public owned sewage treatment works contained 2-vinylpyridine at an average concn of 68 mg/l; and the extract from wastewater of a rubber processing facility contained 2-vinylpyridine at an average concn of 209 mg/l(1).
Packaging and Labelling:
Do not transport with food and feedstuffs.
Soil Adsorption/Mobility:
The Koc of 2-vinylpyridine is estimated as 160(SRC), using a measured log Kow of 1.54(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-vinylpyridine is expected to have moderate mobility in soil. The pKa of 2-vinylpyridine is 4.98(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 2-vinylpyridine is expected to be greater in acidic soils(SRC).
Non-Human Toxicity Values:
LD50 GUINEA PIG PERCUTANEOUS LESS THAN 0.5 ML/KG
Peroxide Forming Chemical:
Reference(s): Kelly
Non-Human Toxicity Excerpts:
MUTAGENIC ACTIVITY COULD NOT BE ADEQUATELY ASSESSED IN SALMONELLA TYPHIMURIUM/MAMMALIAN MICROSOME SYSTEM USING STRAINS TA1535, TA98 & TA100 WITH & WITHOUT S-9 MIX BECAUSE OF SEVERE TOXICITY.
Artificial Pollution Sources:
2-Vinylpyridine's production and use as a monomer for polyvinylpyridine polymers used as tire-cord binders(1), in synthetic rubbers, photographic film, ion exchange resins as well as in pharmaceuticals(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation:
AEROBIC: 2-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).
Effects of Long Term Exposure:
Repeated or prolonged contact may cause skin sensitization.
Hazard Classes and Categories:
Hazardous to the aquatic environment (Long-term) - Category 2
Effects of Short Term Exposure:
The substance may cause effects on the skin. This may result in delayed burns. The substance is severely irritating to the eyes and respiratory tract.
Environmental Bioconcentration:
An estimated BCF of 3 was calculated for 2-vinylpyridine(SRC), using a log Kow of 1.54(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-vinylpyridine is estimated as 3.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-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 10 hours(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 80 days(SRC). 2-Vinylpyridine's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). However, 2-vinylpyridine is a weak base with a pKa of 4.98(4), which indicates this compound will partially exist in the protonat...
Antidote and Emergency Treatment:
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/
Shipment Methods and Regulations:
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.
Environmental Abiotic Degradation:
The rate constant for the vapor-phase reaction of 2-vinylpyridine with photochemically-produced hydroxyl radicals has been measured as 5.67X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 6.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2-vinylpyridine with ozone has been estimated as 2.1X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(2). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(3). 2-Vinylpyridine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(4). Data are not available to assess thi...
Probable Routes of Human Exposure:
The most probable human exposure to 2-vinylpyridine would be occupational exposure, which may occur through dermal contact or inhalation at places where it is produced or used. Non-occupational exposures are likely to occur from the passive and active inhalation of cigarette smoke(1).
Other Environmental Concentrations:
2-Vinylpyridine was detected in cigarette smoke at an average concn of 32 nmol/cu m/cigarette in a test chamber(1).
Environmental Fate/Exposure Summary:
2-Vinylpyridine's production and use as a monomer for polyvinylpyridine polymers used as tire-cord binders, in synthetic rubbers, photographic film, ion exchange resins as well as in pharmaceuticals may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 2.6 mm Hg at 25 °C indicates 2-vinylpyridine will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-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 6.8 and 13 hours, respectively. If released to soil, 2-vinylpyridine is expected to have moderate mobility based upon an estimated Koc of 160. 2-Vinylpyridine has a pKa of 4....
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/
Shipping Name/ Number DOT/UN/NA/IMO:
IMO 6.1; Vinylpyridines, inhibited
Skin, Eye, and Respiratory Irritations:
BRIEF EXPOSURES TO UNDETERMINED CONCN ... CAUSED EYE, NOSE, & THROAT IRRITATION ... .

Production methods and uses

Production method
Alpha-picoline + formaldehyde (condensation/dehydration)
purpose
Uses:
2-Vinylpyridine is a large-volume specialty chemical used primarily for manufacturing terpolymers, e.g., styrene, butadiene, and vinylpyridine, used to coat fabric cords of tires and fabric-reinforced rubber products, such as belts.
Industry Uses:
Intermediate
General Manufacturing Information:
Industry Processing Sectors: Synthetic Rubber Manufacturing

Related

upstream information
Methods of Manufacturing:
Alpha-picoline (CID:7975); formaldehyde (CID:712); sodium hydroxide (CID:14798); 2-(2-pyridyl)ethanol (CID:7675); 2-vinylpyridine (CID:7521)
downstream information

No downstream information yet

MSDS

Found 0 shareMSDS