HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Isopropenylacetat
1-PROPEN-2-OL ACETATE · Propen-2-yl acetate · 1-Acetoxy-1-methylethylene · ACETIC ACID ISOPROPENYL ESTER · 2-Acetoxypropene · Isopropyl Acrtate · 2-Acetoxypropylene · propen-2-ylacetate
Identifikatoren & physikalische Daten
| CAS No. | 108-22-5 |
|---|---|
| Summenformel | C5H8O2 |
| Durchschnittliche Molmasse | 100,12 g/mol |
| Monoisotopische Masse | 100,0524295 g/mol |
| SMILES | C=C(C)OC(C)=O |
| InChIKey | HETCEOQFVDFGSY-UHFFFAOYSA-N |
| PubChem CID | 7916 |
| ChEMBL | CHEMBL1385681 |
| ChEBI | CHEBI:173340 |
| EC No. | 203-562-7 |
| DTXSID | DTXSID3031492 |
| Lokaler Name | Isopropenylacetat |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 94,3 |
| Stoffklassen | Other Classes -> Esters, OtherFlammable agents - 3rd degree |
| SpringerMaterials Properties | Boiling point |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.9090 g/cu cm at 20 °C0.922 g/mL at 20 °C 0.909 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | WATER WHITE LIQUID |
| Löslichkeit | Soluble in ethanol and acetone, very soluble in ethyl ether.Solubility in water 3.25% by weight.34g/l34 g/L (20 ºC) |
| Flammpunkt | 60 °F (NFPA, 2010)15.5 °C60 °F (16 °C) (CLOSED CUP)66 °F |
| Siedepunkt | 97 °C94 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -92.9 °C-93 °C |
| Dampfdruck | 45.2 [mmHg]45 mm Hg at 25 °C23 hPa (20 °C) |
| FEMA | 4152 | ISOPROPENYL ACETATE |
| Brechungsindex | n20/D 1.401(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to very slightly yellow |
| pH | 3 (34g/l, H2O, 20℃) |
| Geruch | at 100.00 %. ethereal acetic fruity sweet berry grape skin |
| Geruchsart | fruity |
| Explosionsgrenze | 1.8%(V) |
| Merck | 14,5203 |
| JECFA Number | 1835 |
| BRN | 1280347 |
| Henry-Konstante | 5.5×10-3 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C5H8O2/c1-4(2)7-5(3)6/h1H2,2-3H3 |
| InChIKey | HETCEOQFVDFGSY-UHFFFAOYSA-N |
| SMILES | CC(=C)OC(C)=O |
| LogP (Verteilungskoeffizient) | 1.28 |
| CAS Datenbank | 108-22-5(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Propen-2-ol, acetate(108-22-5) |
| EPA chemische Informationen | Isopropenyl acetate (108-22-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 300 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1-Propen-2-ol, acetateCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 16-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/17298Isopropenyl acetate: 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.) |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | ...DANGEROUS FIRE RISK. |
| Gesundheitsgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]:· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | A mild irritantNarcotic in high concentrations[Merck Index] May be toxic by inhalation and skin absorption[CAMEO] Inhalation of high concentrations can cause CNS depression[CHEMINFO] A mild to moderate irritant[MSDSonline] Isopropenyl acetate (UN2403) has warning of explosive polymerization[ERG 2016] |
| DOT-Nummer und Handbuch | 2403 129P |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | ISOPROPENYL ACETATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. |
| DOT Emergency Guidelines | /GUIDE 129P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ 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 confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "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./GUIDE 129P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may 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./GUIDE 129P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ 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./GUIDE 129P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.For more DOT Emergency Guidelines (Complete) data for 1-PROPEN-2-OL, ACETATE (8 total), please visit the HSDB record page. |
| DOT Hazard Classification | Isopropenyl acetateUN2403Class 3 Flammable and combustible liquid (49 eCFR § 173.120)PG II: the degree of danger presented by the material is medium |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]: |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]:General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).10.0 [ppm] |
| Brandbekämpfungsverfahren | Alcohol foam. Water may be ineffective. |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]: |
| Entsorgungsverfahren | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)polymerization hazard]: |
| Emergency Response Planning Guidelines | CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from an estimated log Kow of 1.3(2,SRC) and a regression-derived equation(3), indicates that isopropenyl acetate is expected to have high mobility in soil(SRC). Volatilization of isopropenyl acetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of isopropenyl acetate from dry soil surfaces may exist(SRC) based on a vapor pressure of 45 mm Hg(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from an estimated log Kow of 1.3(2,SRC) and a regression-derived equation(3), indicates that isopropenyl acetate is not expected to adsorb to suspended solids and sediment in water(SRC). Isopropenyl acetate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.8X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 3.4 hours and 4.1 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 5.5(3,SRC), from an estimated log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Estimated hydrolysis half-lives of 300 and 30 days at pHs 7 and 8, respectively(6), indicate that hydrolysis is not expected to be an important process(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropenyl acetate, which has a vapor pressure of 45 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropenyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC)the half-lives for these reactions in air are estimated to be about 7.5 and 24 hours, respectively(3,SRC). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Soil Adsorption/Mobility | The Koc of isopropenyl acetate is estimated as approximately 120(SRC), using an estimated log Kow of 1.3(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that isopropenyl acetate is expected to have high mobility in soil(SRC). |
| Human Toxicity Excerpts | MILD IRRITANT. .../CNS DEPRESSANT/ IN HIGH CONCENTRATIONS. |
| Artificial Pollution Sources | Isopropenyl acetate's use as a reagent for acylation of enols(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF of 5.5 was calculated for isopropenyl acetate(SRC), using an estimated log Kow of 1.3(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests that bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for isopropenyl acetate is estimated as 1.8X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that isopropenyl acetate is expected to volatilize rapidly from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 3.4 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 4.1 days(2,SRC). Isopropenyl acetate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of isopropenyl acetate from dry soil surfaces may exist(SRC) based on a vapor pressure of 45 mm Hg(3). |
| Non-Human Toxicity Excerpts | THREE OF SIX RATS DIED FOLLOWING INHALATION OF 4,000 PPM FOR 4 HR. IT CAUSED SLIGHT SKIN IRRITATION IN RABBITS. /FROM TABLE/ |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of isopropenyl acetate with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 7.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the vapor-phase reaction of isopropenyl acetate with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(1,SRC). This corresponds to an atmospheric half-life of about 24 hours at an atmospheric ozone concn of 7X10+11 cu cm/molecule-sec at 25 °C(1,SRC). A base-catalyzed second-order hydrolysis rate constant of 0.27 L/mol-sec(SRC) was estimated using a structure estimation method(2)this corresponds to half-lives of 300 and 30 days at pH values of 7 and 8, respectively(2,SRC). |
| Probable Routes of Human Exposure | Occupational exposure to isopropenyl acetate may occur through inhalation and dermal contact with this compound at workplaces where isopropenyl acetate is produced or used. (SRC) |
| Environmental Fate/Exposure Summary | Isopropenyl acetate's use as a reagent for acylation of enols may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 45 mm Hg at 25 °C indicates isopropenyl acetate is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropenyl acetate will be degraded in the atmosphere by reaction with ozone and photochemically-produced hydroxyl radicalsestimated half-lives for these reactions are 24 and 7.5 hours, respectively. If released to soil, isopropenyl acetate is expected to have high mobility based upon an estimated Koc of 120. Volatilization from wet soil surfaces is expected to occur based on an estimated Henry's Law constant of 1.8X10-3 atm-cu m/mole. This compound's vapor pressure indicates that volatilization from dry soil surfaces may potentially occur. If released into water, adsorption to suspended solids and sediment in the water column is not expected given the estimated Koc for this compound. Volatilization from water surfaces is expected based upon this compound's Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 3.4 hours and 4.1 days, respectively. The potential for bioconcentration in aquatic organisms is low based upon the estimated BCF of 5.5. Hydrolysis is not expected to be an important process based upon estimated half-lives of 300 and 30 days at pHs 7 and 8, respectively. Occupational exposure to isopropenyl acetate may occur through inhalation and dermal contact with this compound at workplaces where isopropenyl acetate is produced or used. (SRC) |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2403 |
| Zollcode | 2915 39 00 |
| RTECS-Nr. | UD4200000 |
| R-Sätze (R) | 11 |
| Toxizität | LD50 orally in rats: 3.0 g/kg (Smyth) |
| Gefahrensymbole | F |
| Sicherheitshinweise (S) | 9-16-29-33 |
| Gefahrenklasse | 3Flam. Liq. 2STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 108-22-5(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 439 °C DIN 51794 |
Anwendungen & Verwendung
Verwenden
Iodine in isopropenyl acetate is a unique catalyst for the acetylation of a variety of alcohols, phenols and amines under solvent free conditions. It is used as a solvent for cellulose, plastics, oil and fats. It is also a building block used for various organic synthesis.