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HCID 81530Erstellt: 27. Oktober 2026

Ethyl cyanoacrylate

cyacrin

https://huagongshe.com/de/chemical/81530

Molekülstruktur von Ethyl cyanoacrylate

Identifikatoren & physikalische Daten

CAS No.25067-30-5
SummenformelC6H7NO2
Durchschnittliche Molmasse125,13 g/mol
Monoisotopische Masse125,04767847 g/mol
SMILESC=C(C#N)C(=O)OCC
InChIKeyFGBJXOREULPLGL-UHFFFAOYSA-N
PubChem CID81530
ChEMBLCHEMBL1564920
EC No.230-391-5
DTXSIDDTXSID1025279

Chemische & physikalische Eigenschaften

XLogP1
Polarare Oberfläche (TPSA)50,1
H-Brücken-Donoren0
H-Brücken-Akzeptoren3
Frei drehbare Bindungen3
Schwere Atome9
Formalladung0
Komplexität175
GeruchStrong , acrid odor
Dichte1.040 at 20 °C
Color/FormClear, colorless, liquid
LöslichkeitSoluble in methyl ethyl ketone, toluene, acetone, DMF /N,N-dimethylformamide/, nitromethane
Flammpunkt82.78 °C (closed cup)75 °C c.c.
Siedepunkt55 °C at 3 mm HgBP: 54-56 °C (0.21-0.40 kPa)
DecompositionWhen heated to decomposition it emits vapors of /Nitrogen oxides/.Decomposition: degradation products include formaldehydethermal decomposition products may include highly toxic fumes of hydrogen cyanide and toxic oxides of carbon and nitrogen
Schmelzpunkt-20 to -25 °C
GeruchsschwelleOdor Threshold Low: 0.31 [ppm]
PolymerizationPolymer: Poly(ethyl 2-cyanoacrylate)PECAPolymerizes rapidly in various media including water
DampfdruckVP: <0.27 kPa at 25 °C0.31 mm Hg at 20 °C<2 mmHg at 25 °C
Surface Tension34.32 dynes/cm
EPA chemische Informationen2-Propenoic acid, 2-cyano-, ethyl ester, homopolymer (25067-30-5)

Sicherheit & Vorschriften

GHS-EinstufungWarningH315: Causes skin irritation [Warning Skin corrosion/irritation]H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Regulatorische InformationenChemical: 2-Propenoic acid, 2-cyano-, ethyl ester2-Propenoic acid, 2-cyano-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-cyano-, ethyl ester 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: 24-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14976Ethyl cyanoacrylate: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
BrandgefahrenCombustible. Above 75 °C explosive vapour/air mixtures may be formed.
GefahrenübersichtCyanoacrylates are rare sensitizers of the skin. [Marks, p. 179] Five patients had asthma provoked by cyanoacrylates[Reference #1] DSEN and RSEN notations recommended[ACGIH]
EG-EinstufungSymbol: XiR: 36/37/38S: (2)-23-24/25-26
Special ReportsWHOConcise International Chemical Assessment Document 36, Methyl Cyanoacrylate and Ethyl Cyanoacrylate (2001). CICADs are concise documents that provide summaries of the relevant scientific information concerning the potential effects of chemicals upon human health and/or the environment. The primary objective of CICADs is characterization of hazard and dose-response from exposure to a chemical.[Available from, as of February 15, 2011: http://www.inchem.org/documents/cicads/cicads/cicad36.htm]

Anwendungen & Verwendung

Verwenden

In adhesives; in manufacture of plastics, electronics, scientific instruments, jewelry, sports equip; in cable joining, manicuring, dentistry, mortuaries, fingerprint development. Polymer nanoparticles as pharmaceutic aid for controlled release drug delivery.

TSCA-AnforderungenSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 1/26/94Reporting date: 3/28/94.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Propenoic acid, 2-cyano-, ethyl ester is included on this list. Effective date: 1/26/94Sunset date: 12/19/95.
Chemical DangersThe substance rapidly polymerizes. Decomposes on heating and on burning. This produces toxic and irritating fumes and gases including nitrogen oxides and cyanides.
Toxic Combustion ProductsHazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx).
Hazard Classes and CategoriesSkin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (99.7%)Eye irritation - category 2Specific target organ toxicity (single exposure) - category 3Skin irritation - category 2Flammable liquids - Category 4Serious eye damage/eye irritation - Category 2BSkin sensitization - Category 1Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)Skin corrosion/irritation - Category 2Serious eye damage/eye irritation - Category 2Flammable agents - 2nd degree, Reactive agents - 2nd degree
BrandbekämpfungIn case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep drums, etc., cool by spraying with water.
Erste-Hilfe-MaßnahmenFresh air, rest. Refer for medical attention.Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Sichere LagerungCool.
BrandbekämpfungsverfahrenSuitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
LagerbedingungenKeep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C Product is sensitive to light and moisture.
ReinigungsverfahrenPersonal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.
Verschüttetes entsorgenVentilation. 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.
Preventive MeasuresHandle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
Eye PreventionWear safety goggles.
Fire PreventionNO open flames. Above 75 °C use a closed system, ventilation and explosion-proof electrical equipment.
Inhalation RiskNo 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.
TreatmentAntidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Gesundheitliche AuswirkungenExposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.8(SRC), determined from a structure estimation method(2), indicates that ethyl cyanoacrylate is expected to have very high mobility in soil(SRC). However, movement of ethyl cyanoacrylate through soil will be hindered by its rapid polymerization as it comes into contact with moisture or other weakly basic substances(3,4). Since ethyl cyanoacrylate polymerizes rapidly on contact with moisture, volatilization from moist soil surfaces is not a relevant environmental process for this substance. Ethyl cyanoacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.31 mm Hg at 20 °C(3).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.8(SRC), determined from a structure estimation method(2), indicates that ethyl cyanoacrylate is not expected to adsorb to suspended solids and sediment(SRC). However, the 2-cyanoacrylate esters polymerize rapidly on contact with moisture or other weakly basic substances(3,4). Therefore, environmental processes such as biodegradation, volatilization from water surfaces and bioconcentration in aquatic organisms are not relevant for this substance(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl cyanoacrylate, which has a vapor pressure of 0.31 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl cyanoacrylate 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 3.5 days(SRC), calculated from its rate constant of 4.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethyl cyanoacrylate contains chromophores that absorb strongly at wavelengths >290 nm, and therefore may be susceptible to direct photolysis by sunlight(4).
Unerwünschte WirkungenSkin Sensitizer - An agent that can induce an allergic reaction in the skin.Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
ExpositionspfadeThe substance can be absorbed into the body by inhalation of its vapour.Oral (L96)inhalation (L96)dermal (L96)
ToxizitätsübersichtOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Signs and SymptomsRedness. Pain.Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of ethyl cyanoacrylate can be estimated to be 6.8(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl cyanoacrylate is expected to have very high mobility in soil. However, movement of ethyl cyanoacrylate through soil will be hindered by its rapid polymerization as it comes into contact with moisture or other weakly basic substances(3,4).
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ 27 patients (26 women and 1 man), all in contact with artificial nails, were tested for acrylic compounds, known to be present in nail cosmetics. The patch test results obtained in these patients demonstrated that 2-hydroxyethyl methacrylate and ethyl cyanoacrylate were the only 2 allergens needed to diagnose contact allergy to acrylic-containing nail cosmetics, except for 1 patient who reacted only to her nail preparation.../CASE REPORTS/ ... A young hairdresser ... developed an occupational allergic contact dermatitis to 2 "instant glues" used to attach false hair. The eczematous eruption involved the fingers and face slightly but mainly the eyelids. Patch test reactions were strongly positive to ethyl cyanoacrylate adhesives./CASE REPORTS/ An apprentice cobbler with an occupational allergic contact dermatitis from an ethyl cyanoacrylate glue, in which the major monomer was shown to be the sensitizer, is reported. Initial patch testing with the cyanoacrylate glue dissolved in acetone with the Finn Chamber (aluminium) technique yielded false-negative reactions. Positive test reactions were obtained with the same preparations using Van der Bend chambers. With petrolatum as vehicle for the glue, there was no difference between Finn Chamber technique and Van der Bend chamber technique. The role of aluminium in the false-negative reactions is discussed./CASE REPORTS/ ... An individual ... showed a skin reaction associated with occupational exposure to an ethyl cyanoacrylate (ECA)-based adhesive (90% ECA), initially on the backs of hands but later progressing to all of the hands, lower arms, and abdomen. The only positive skin reaction in a patch testing series was to ECA. Negative reactions were reported for a group of 20 control subjects patch-tested with 100% adhesive.For more Human Toxicity Excerpts (Complete) data for Ethyl cyanoacrylate (29 total), please visit the HSDB record page.
Artificial Pollution SourcesEthyl cyanoacrylate's production and use as an adhesive(1,2) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationEthyl cyanoacrylate polymerizes rapidly on contact with moisture(1,2). Therefore, biodegradation is not a relevant environmental fate process for this substance(SRC).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
TSCA-Inventar-StatusTSCA listed