ポリ-4-ビニルピリジン, ビーズ無水

4-Vinylpyridine

HCID 7502CAS 100-43-6

基本情報

標準SMILES
C=Cc1ccncc1
InChIKey
KFDVPJUYSDEJTH-UHFFFAOYSA-N
分子式
C7H7N
平均分子量
105.14 g/mol
単同位体質量
105.05784923

名称と識別子

優先名称
4-Vinylpyridine
IUPAC
4-ethenylpyridine
現地名
4-ビニルピリジン
英語名
4-Vinylpyridine
分子式
C7H7N
分子量
105.14

名称と別名

4-VINYLPYRIDINE100-43-64-EthenylpyridinePyridine, 4-ethenyl-Pyridine, 4-vinyl-gamma-VinylpyridineDTXSID0051499I56G67XM8DNSC-18256DTXCID4030047RefChem:6770202-852-0
名称をさらに表示
4-ビニルピリジン1-(4-ピリジニル)エテン4-エテニルピリジン4ビニルピリジン4‐ビニルピリジン4VPPyridine,4-ethenyl-4-vinylpyridine monomer4-vinyl-pyridinVinylpyridine,4-4-ethenyl-pyridin4-Pyridylethylene
684-212-4.gamma.-VinylpyridineCHEMBL4550330NSC18256CCRIS 5240HSDB 15094-Vinylpyridine (stabilized with hydroquinone)EINECS 202-852-0

データベース識別子

CAS
100-43-6、25232-41-1
PubChem CID
7502
DTXSID
DTXSID0051499
ChEMBL
CHEMBL4550330
UNII
I56G67XM8D
EC Number
202-852-0、684-212-4
Nikkaji
J38.337F

物性

構造計算による物性

XLogP
1.6
極性表面積
12.9 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
1
重原子数
8

実験および物理化学的性質

OdorPungent unpleasant odor
Density0.9800 @ 20 °C/4 °C
Color/FormRED TO DARK BROWN LIQUID
Solubility · 2 件

Soluble in alcohol and chloroform; slightly soluble in ether

In water, 29,100 mg/l @ 20 °C

Boiling Point65 °C @ 15 mm Hg
Decomposition · 2 件

DECOMPOSITION BY HEAT IS ACCOMPANIED BY RELEASE OF DANGEROUS CYANIDE FUMES.

When heated to decomp ... emits toxic fumes of /nitrogen oxides/.

物理化学的性質

融点
25 °C · <25 °C
沸点
62 · 62-65 °C/15 mmHg (lit.)
比重(密度)
0.975 g/mL · 0.975 g/mL at 25 °C (lit.)
蒸気圧
2.28 hPa · 2.28hPa at 25℃
屈折率
20 · n20/D 1.549(lit.)
闪点
125 °F · 125 °F
化学的性質 · 1 件

化学的特性dark brown to yellow liquid. 2.9g can be dissolved in 100g of water at 20℃, soluble in methanol, ether, benzene, acetone, and slightly soluble in ether. When exposed to light and heat, polymerization occurs, and 0.1%-0.2% hydroquinone is often added as a polymerization inhibitor during storage.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 16.6% (37 of 223) of reports.

Danger

H226 (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.

危険有害性情報

Regulatory Information · 4 件

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/10126

4-Vinylpyridine: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFire hazard is moderate ... .
Hazards Summary · 1 件

Irritating to eyes, nose, and throat; Causes 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 · 5 件

/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.

Hazard Classes and Categories · 3 件

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 3;Acute toxicity (Oral) - Category 3;Acute toxicity (Inhalation: Vapours) - Category 1;Skin corrosion/irritation - Category 2;Serious eye damage/eye irritation - Category 2A;Skin sensitization - Category 1;Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation);Hazardous to the aquatic environment (Acute) - Category 1;Hazardous to the aquatic environment (Long-term) - Category 1

Shipment Methods and Regulations · 3 件

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.

安全と保護具

Disposal Methods · 1 件

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 · 4 件

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.

Personal Protective Equipment (PPE) · 1 件

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/

毒性情報

Environmental Fate · 3 件

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 EffectsDermatotoxin - 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 · 1 件

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 · 4 件

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 · 1 件

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 BiodegradationAEROBIC: 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).

法規制情報

Regulatory Information · 4 件

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/10126

4-Vinylpyridine: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F
8-10
wgk
3
tsca
TSCA listed
rtecs
UU1045000
ridadr
UN 3073 6.1/PG 2
hs_code
29333990

化学と産業

薬理情報

MeSH Pharmacological Classification · 1 件

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 &amp; Hackh&apos;s Chemical Dictionary, 5th ed, p301, p499)

Absorption, Distribution and Excretion · 3 件

... /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/

用途と製造

Uses · 4 件

Used to make poly(4-vinylpyridine), elastomers, and pharmaceuticals; [HSDB] Used as a monomer; [Kanerva, p. 1845]

Used as a chemical intermediate for the synthesis of poly(4-vinylpyridine)

Elastomers and pharmaceuticals. Latex used as tire cord binder (41% solids). The latex is copolymerized with butadiene-styrene /vinylpyridine/

The cross-linked resin made from 4-vinyl pyridine and divinylbenzene has been used to remove poisonous hexavalent chromium ions from wastewater...the poly(4-vinylpyridines) are used as ion-exchange membranes and electrodes for reversible cells...4,4'-(1,3-propanediyl)bispiperidine, made from 4-vinylpyridine is used as a raw material for polyamide resins and 2-(4-pyridyl)ethylsulfonic acid from 4-vinylpyridine is a coagulation accelerator for the gelatin layer of photographic plates.

U.S. Production · 2 件

2023: 250,000 - <550,000 lb;2022: 550,000 - <1,000,000 lb;2021: 250,000 - <550,000 lb;2020: 250,000 - <550,000 lb

Although 4-vinylpyridine has been used for various purposes, its total annual demand is presumed to be only several hundred tons.

Industry UsesIntermediate
Methods of Manufacturing · 2 件

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.

General Manufacturing Information · 4 件

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.

応用分野 · 3 件

用途繊維改質剤,ゴム改質剤,接着剤,高分子系界面活性剤およびイオン交換体等の機能性高分子の原料モノマー

用途有機合成原料(イオン交換膜)。

使用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.

調製方法 · 2 件

製造方法4-Vinylpyridine is synthesized by reacting 4-picoline with formaldehyde to generate 4-pyridineethanol, which is then dehydrated.

純化方法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.]

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