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1-Butoxy-2,3-epoxy-propan
BGE · N-BUTYL GLYCIDYL ETHER · NBGE · 1-BUTOXY-2,3-EPOXYPROPANE · NORMAL-BUTYLGLYCIDYL ETHER · Oxirane, 2-(butoxymethyl)- · n-Butyl glycidyl ether (BGE) · tk10408
Identifikatoren & physikalische Daten
| CAS No. | 2426-08-6 |
|---|---|
| Summenformel | C7H14O2 |
| Durchschnittliche Molmasse | 130,18 g/mol |
| Monoisotopische Masse | 130,09937969 g/mol |
| SMILES | CCCCOCC1CO1 |
| InChIKey | YSUQLAYJZDEMOT-UHFFFAOYSA-N |
| PubChem CID | 17049 |
| ChEMBL | CHEMBL1530010 |
| EC No. | 219-376-4 |
| DTXSID | DTXSID9024691 |
| Lokaler Name | 1-Butoxy-2,3-epoxy-propan |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 21,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 73,3 |
| Stoffklassen | Flammable agents - 2nd degree |
| Polymers | Plastics & Rubber -> Glycidyl Ethers |
| LogP (Verteilungskoeffizient) | log Kow = 0.63 |
| Geruch | Irritating odor |
| Dichte | 0.91 (USCG, 1999) - Less dense than waterwill float0.908 g/cu cm at 25 °CRelative density (water = 1): 0.910.918 @ 20°C0.91 g/mL at 25 °C(lit.) |
| Color/Form | Clear, colorless liquid |
| Löslichkeit | 10 to 50 mg/mL at 72 °F (NTP, 1992)In water, 20,000 mg/L at °CSolubility in water, g/100ml at 20 °C: 22%20g/l2 g/100 mL |
| Flammpunkt | 130 °F (NTP, 1992)54 °C54 °C (closed cup)54 °C c.c.132 °F |
| Siedepunkt | 327 °F at 760 mmHg (NTP, 1992)164 °C169 °C @760 [mm Hg]164-166 °C(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes.The substance decomposes on exposure to light and air. |
| Dampfdichte | 3.78 at 25 °C (Air = 1)Relative vapor density (air = 1): 3.78 |
| Dampfdruck | 3.2 mmHg at 77 °F (NTP, 1992)3.2 [mmHg]3.2 mm Hg at 25 °CVapor pressure, kPa at 25 °C: 0.433 mmHg at 77 °F3.2 [mm Hg] @25 °C5 hPa (20 °C) |
| Schmelzpunkt | 59 °C |
| Brechungsindex | n20/D 1.418(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| BRN | 103668 |
| Henry-Konstante | 4.0×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. May form explosive peroxides on contact with air. Store under inert gas. |
| InChI | 1S/C7H14O2/c1-2-3-4-8-5-7-6-9-7/h7H,2-6H2,1H3 |
| InChIKey | YSUQLAYJZDEMOT-UHFFFAOYSA-N |
| SMILES | CCCCOCC1CO1 |
| LogP (Verteilungskoeffizient) | 0.63 at 25℃ |
| CAS Datenbank | 2426-08-6(CAS DataBase Reference) |
| NIST chemische Informationen | Oxirane, (butoxymethyl)-(2426-08-6) |
| EPA chemische Informationen | n-Butyl glycidyl ether (2426-08-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P318, P319, P321, P330, P333+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Oxirane, (butoxymethyl)-Hazard Traits - CarcinogenicityTP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 15-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/22306Butyl glycidyl ether: 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Aliphatic and allyl glycidyl ethers: Human health tier II assessment |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Special Hazards of Combustion Products: May form explosive peroxides upon contact with air. Toxic fumes such as carbon monoxide may be produced.Flammable. Above 54 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable |
| Gesundheitsgefahren | Exposure can cause mild irritation of skin, eyes, nose, and respiratory tract. Chronic exposure may cause inflammation and sensitization of the skin. (USCG, 1999) |
| Gefahrenübersicht | Repeated or prolonged contact may cause skin sensitization. [ICSC] BGE causes testicular atrophy in male rats exposed to levels of 75 ppm or higher for 10 weeks. Potential for dermal sensitization[ACGIH] Causes pulmonary edema in high dose animal studies[Reference #1] |
| Reaktive Gruppe | Ethers |
| EG-Einstufung | Symbol: XnR: 10-20/22-37-40-43-68-52/53S: (2)-24/25-36/37-61 |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: III |
| TSCA-Anforderungen | 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. Oxirane, (butoxymethyl)- is included on this list. |
| Reactivity Alerts | Highly Flammable |
| Brandbekämpfung | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.(General first aid procedures) |
| Sichere Lagerung | Fireproof. Separated from strong oxidants, strong bases, strong acids and amines. Cool. Keep in the dark. |
| Brandbekämpfungsverfahren | In case of fire: keep drums, etc., cool by spraying with water./Use/ water spray, foam, powder, carbon dioxideIf material on fire or involved in fire: Use water in flooding quantities. Use foam, dry chemical, or carbon dioxide. Apply water from as far a distance as possible. Cool all affected containers with flooding quantities of water. Solid streams of water may spread fire. Keep run-off water out of sewers and water sources. |
| Lagerbedingungen | Fireproof. Separated from strong oxidants, strong bases, strong acids. Cool. Keep in the dark. |
| Reinigungsverfahren | Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.Environmental considerations: Land Spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil. sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.Environmental considerations: Water Spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction.Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | 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.Where there is any possibility of a worker's eyes being exposed to BGE, an eye-wash fountain should be provided within the immediate work area for emergency use. ...Where there is any possibility of a worker's body being exposed to BGE, facilities for quick drenching of the body should be provided within the immediate work area for emergency use. ...The worker should immediately wash the skin when it becomes contaminated.For more Preventive Measures (Complete) data for N-BUTYL GLYCIDYL ETHER (10 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| Zielorgane | Eyes, skin, respiratory system, central nervous system, blood |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 52(SRC), determined from a log Kow of 0.63(2) and a regression-derived equation(3), indicates that n-butyl glycidyl ether is expected to have high mobility in soil(SRC). Volatilization of n-butyl glycidyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 3.2 mm Hg(4), and water solubility of 2X10+4 mg/L(5). The potential for volatilization of n-butyl glycidyl ether from dry soil surfaces exists(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2005).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 52(SRC), determined from a log Kow of 0.63(2) and a regression derived equation(3), indicates that n-butyl glycidyl ether 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 2.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 3.2 mm Hg(4), and water solubility of 2X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 and 16 days, respectively (SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). n-Butyl glycidyl ether contains an epoxide functional group which is susceptible to hydrolysis, but the rate of this reaction is very slow based upon an estimated half-life of over 60 years at pH 7(8). Biodegradation data were not available(SRC, 2005).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyl glycidyl ether, which has a vapor pressure of 3.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyl glycidyl ether 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 19 hours(SRC), calculated from its rate constant of 2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). |
| Unerwünschte Wirkungen | Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Sore throat.Redness. Pain.irritation eyes, skin, noseskin sensitizationnarcosispossible hematopoietic effectscentral nervous system depression |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2426-08-6] |
| Soil Adsorption/Mobility | The Koc of n-butyl glycidyl ether is estimated as 52(SRC), using a log Kow of 0.63(1) and a regression-derived equation(2). According to a classification scheme(2), this estimated Koc value suggests that n-butyl glycidyl ether is expected to have high mobility in soil(SRC). |
| TSCA Test Submissions | Glycidyl n-butyl ether was evaluated for the ability to increase the incidence of micronuclei in bone marrow cells of female B6D2F1 mice treated by oral gavage. Ten mice received 1000 mg/kg of the test article (in corn oil) 1x daily for 5 daysanimals were sacrificed 4 hours following the final dose. The percentage of cells with micronuclei was not statistically significantly (Dunnett's t-test, p > 0.1) increased compared to controls. The toxicity of glycidyl n-butyl ether to mice at the level tested was not reported.In a modified dominant lethal and pathology study, mature male B6D2F1 mice were mated with 3 virgin females each. After pre-treatment matings, the males (2 groups/dose level, 20 and 10 males/group) were treated with glycidyl n-butyl ether by dermal application on clipped skin at dose levels of 0, 0.375, 0.75 or 1.5 g/kg/day, 3 times/week for 8 weeks. Two groups of unclipped male mice (10 and 20/group) served as controls. After the treatment period, males and females were mated for 3 weeks. Males were sacrificed following final mating period and females were sacrificed 14 days after the midweek of their mating periods. Variables were analyzed with respect to group differences by dose (dose), overall time period differences (time), and the dose group by time period interaction (dose/time). Significant differences were observed between treated and control animals in the following: decreased pregnancy rates (dose basis, excluding controls), increased implants/pregnant female (time basis, after 1st pre-treatment period with trend back to control value at (3rd post-treatment period), decreased proportion of dead implants (dose and dose/time bases), increased incidence of necrosis of the epidermis at point of application (high-dose group). No significant differences were observed between treated and control animals in the following: pregnancy rates, gross pathology of males, histopathology of the liver, lung, and testes, and numbers of dead cells and necrotic tubules.The mutagenicity of glycidol n-butyl ether (GBE) was evaluated in Salmonella tester strains TA1535 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, GBE, diluted with DMSO, was tested for mutagenicity at concentrations up to 2000 ug/plate using the plate incorporation method. GBE caused a positive response in bacterial tester strain TA1535 at 2000 ug/plate, both with and without metabolic activation, and in bacterial tester strain TA1538 at concentrations of 100 ug/plate and higher without activation and at 500 ug/plate and higher with activation.The mutagenicity of glycidol n-butyl ether (GBE) was evaluated in male B6D2F1 mice (at least 10) dermally exposed to GBE at a dose level of 1.5 g/kg three times/week for a minimum of 8 weeks. Following the treatment period, the male mice were mated with 3 untreated virgin female B6D2F1f mice for one week and mated with 3 fresh females for a second week. Significant differences were observed between pre- and post-treatment results in the following: proportion of deaths/pregnancy (increased during post-treatment period), number of implants/pregnancy (decreased post-treatment), and percent pregnancy (increased post-treatment).For more TSCA Test Submissions (Complete) data for N-BUTYL GLYCIDYL ETHER (7 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Appreciable skin irritation and sensitization have been reported in humans./SIGNS AND SYMPTOMS/ Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl and diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl and diglycidyl ethers//SIGNS AND SYMPTOMS/ Long-term (chronic): Exposure to BGE can cause inflammation and sensitization of the skin./SIGNS AND SYMPTOMS/ N-butyl glycidyl ether possesses satisfactory warning properties. Odor of vapors is not unpleasant but leads to irritation.For more Human Toxicity Excerpts (Complete) data for N-BUTYL GLYCIDYL ETHER (8 total), please visit the HSDB record page. |
| Artificial Pollution Sources | n-Butyl glycidyl ether's production and use as a viscosity reducing agent, stabilizer for chlorinated solvents(1), reactive diluent for epxoy resins(2), and chemical intermediate (1) may result in its release to the environment through various waste streams(SRC). |
| Carcinogen Classification | 1-Butyl glycidyl etherGroup 2B: Possibly carcinogenic to humansVolume 125: (2020) Some Industrial Chemical Intermediates and Solvents2020 online2019 |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated for n-butyl glycidyl ether(SRC), using a log Kow of 0.63(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). |
| F | 9-21 |
| Arbeitsplatzgrenzwert (OEL) | Ceiling: 5.6 ppm (30 mg/m3) [15-minute] |
| Wassergefährdungsklasse (WGK) | 2 |
| Sofort lebensgefährliche Konzentration | 250 ppm |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3271 3/PG 3 |
| Zollcode | 29109000 |
| RTECS-Nr. | TX4200000 |
| R-Sätze (R) | 10-20/22-37-40-43-52/53-68-20/21/22-45-36/37/38-23/24/25 |
| Toxizität | LD50 orally in Rabbit: 1660 mg/kg LD50 dermal Rabbit 2520 mg/kg |
| Gefahrensymbole | Xn,T |
| Sicherheitshinweise (S) | 24/25-36/37-61-45-53-26 |
| Gefahrenklasse | 3Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Carc. 1BEye Dam. 1Flam. Liq. 3Muta. 2Repr. 2Skin Corr. 1BSkin Sens. 1STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 2426-08-6(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 215 °C |
Anwendungen & Verwendung
Beschreibung
n-Butyl glycidyl ether is a reactive diluent used to reduce viscosity of epoxy res ins Bisphenol A type.
Verwenden
Uses include the roles of viscosity-reducing agent for easier handling of conventional epoxy resins, acid acceptor for stabilizing chlorinated solvents, and chemical intermediate. Some curing agents may produce hazardous polymerizations in large quantities.