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1,1-Dimethoxyethan
DIMETHYL ACETAL · ACETALDEHYDE DIMETHYL ACETAL · FEMA 3426 · Ethane,1,1-dimethoxy- · CH3CH(OCH3)2 · methylformyl · dimethylaldehyde · Dimethyl aldehyde
Identifikatoren & physikalische Daten
| CAS No. | 25154-53-4 |
|---|---|
| Summenformel | C4H10O2 |
| Durchschnittliche Molmasse | 90,12 g/mol |
| Monoisotopische Masse | 90,06807956 g/mol |
| SMILES | COC(C)OC |
| InChIKey | SPEUIVXLLWOEMJ-UHFFFAOYSA-N |
| PubChem CID | 10795 |
| ChEMBL | CHEMBL3183607 |
| ChEBI | CHEBI:178404 |
| EC No. | 208-589-8 |
| DTXSID | DTXSID7027178 |
| Lokaler Name | 1,1-Dimethoxyethan |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 18,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 24,7 |
| Stoffklassen | Other Classes -> AcetalsFlammable agents - 3rd degree |
| SpringerMaterials Properties | Boiling point |
| Geruch | STRONGLY AROMATIC ODORGREEN VEGETABLE ODOR |
| Geschmack | FRUITY TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.85015 @ 20 °C/4 °C0.850-0.8600.852 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | COLORLESS LIQMOBILE LIQ |
| Löslichkeit | ETHERVERY SOL IN ACETONEMiscible with water, alcohol, chloroform, ether.1000 mg/mL at 25 °Cmiscible with water, organic solvent, oilsmiscible (in ethanol)Chloroform (Sparingly)Soluble |
| Flammpunkt | BELOW 80 °F1 °F |
| Siedepunkt | 64.5 °C64.00 to 65.00 °C. @ 760.00 mm Hg64 °C64 °C(lit.) |
| Schmelzpunkt | -113.2 °C-113 °C |
| Dampfdichte | 3.1 (vs air) |
| Dampfdruck | 200 hPa (20 °C) |
| FEMA | 3426 | 1,1-DIMETHOXYETHANE |
| Brechungsindex | n20/D 1.367(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Oil |
| Farbe | Colourless |
| Geruch | at 1.00 % in propylene glycol. sharp sweet alcohol ether green new mown hay |
| Geruchsart | ethereal |
| Biologische Quelle | synthetic |
| Merck | 14,3226 |
| JECFA Number | 940 |
| BRN | 1697039 |
| Henry-Konstante | 1.5×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielektrizitätskonstante | 3.4900000000000002 |
| InChI | 1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 |
| InChIKey | SPEUIVXLLWOEMJ-UHFFFAOYSA-N |
| SMILES | COC(C)OC |
| LogP (Verteilungskoeffizient) | 0.63 at 25℃ |
| CAS Datenbank | 534-15-6(CAS DataBase Reference) |
| NIST chemische Informationen | Ethane, 1,1-dimethoxy-(534-15-6) |
| EPA chemische Informationen | 1,1-Dimethoxyethane (534-15-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Ethane, 1,1-dimethoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Ethane, 1,1-dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,1-dimethoxy- 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: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/255131,1-Dimethoxyethane: 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 127 [Flammable Liquids (Water-Miscible)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | FLAMMABLE, DANGEROUS FIRE RISK. |
| Gesundheitsgefahren | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· Inhalation or contact with material may irritate or burn skin and eyes. |
| Gefahrenübersicht | A severe skin and eye irritant[CAMEO] Acts as general anesthetic in lethal-dose inhalation studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] A fire hazard[Hawley] An irritant[MSDSonline] |
| DOT-Nummer und Handbuch | 2377 127 |
| Reaktive Gruppe | Ethers |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | 1,1-DIMETHOXYETHANE may react violently with strong oxidizing agents. Can act as a weak base to form salts with strong acids and addition complexes with Lewis acids. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert. |
| DOT Emergency Guidelines | /GUIDE 127: FLAMMABLE LIQUIDS (Polar/Water-Miscible)/ 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 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./GUIDE 127: FLAMMABLE LIQUIDS (Polar/Water-Miscible)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution./GUIDE 127: FLAMMABLE LIQUIDS (Polar/Water-Miscible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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 127: FLAMMABLE LIQUIDS (Polar/Water-Miscible)/ 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 1,1-DIMETHOXYETHANE (8 total), please visit the HSDB record page. |
| DOT Hazard Classification | 1,1-DimethoxyethaneUN2377Class 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 127 [Flammable Liquids (Water-Miscible)]: |
| 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 127 [Flammable Liquids (Water-Miscible)]:General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Do not extinguish fire unless flow can be stopped. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius. |
| Freisetung ohne Brand | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| 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. |
| Preventive Measures | If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amount of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.Evacuation: ... If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions. |
| Isolation and Evacuation | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective gloves, boots and goggles. |
| 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 recommended classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,1-dimethoxyethane will have very high mobility in soil(SRC). Volatilization of 1,1-dimethoxyethane may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.7X10-5 atm-cu m/mole(3,SRC), and from dry soil surfaces(SRC), based on an experimental vapor pressure of 171 mm Hg(4). According to one study, 1,1-dimethoxyethane shows a slight ability to support growth for an organism isolated from soil enriched with triethylene glycol(5).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,1-dimethoxyethane would not adsorb to suspended solids and sediment(SRC) in the water. 1,1-Dimethoxyethane would volatilize from water surfaces based on an estimated Henry's Law constant of 6.7X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 15 hours and 7.5 days, respectively(4,SRC). An estimated BCF value of 0.86(4,SRC), from an estimated log Kow(5,SRC), suggests that 1,1-dimethoxyethane will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(6). According to one study, 1,1-dimethoxyethane shows a slight ability to support growth for an organism isolated from soil enriched with trietylene glycol(7).ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 171 mm Hg at 25 °C(2) indicates that 1,1-dimethoxyethane will exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,1-dimethoxyethane 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 about 43 hours(3,SRC). Vapor-phase 1,1-dimethoxyethane may be physically removed from the air by wet deposition because of its high water solubilty(4). |
| Lebensmitteluntersuchungswerte | 1,1-Dimethoxyethane was identified as a volatile component of beef(1). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indexes(1), the Koc for 1,1-dimethoxyethane can be estimated to be about 1(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that 1,1-dimethoxyethane has very high mobility in soil(SRC). |
| Natural Pollution Sources | IN RASPBERRY AND BLACKBERRY, STRAWBERRY, HOP OIL, COFFEE, TEA. |
| Human Toxicity Excerpts | MODERATELY TOXIC BY INGESTION AND INHALATION. |
| Artificial Pollution Sources | 1,1-Dimethoxyethane's production and use in medicine(1), organic synthesis(1), in Mering's mixture (2 vol 1,1-dimethoxyethane and 1 vol chloroform)(2), and as a flavoring ingredient(3) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | An aerobic biodegradation study using gram-negative asporogenous rod bacteria isolated from soil enriched with triethylene glycol exhibited borderline growth (scarcely detectable growth, not reproducible) with 1,1-dimethoxyethane(1). |
| Environmental Bioconcentration | An estimated BCF value of 0.86 was calculated for 1,1-dimethoxyethane(SRC), using an estimated log Kow of 0.22(1,SRC) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be an low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 1,1-dimethoxyethane is estimated as 6.7X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1,1-dimethoxyethane will volatilize from water surfaces(2,SRC). 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) is estimated as approximately 15 hours(2,SRC). The 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 7.5 days(2,SRC). 1,1-Dimethoxyethane's high vapor pressure, 171 mm Hg(3) indicates that volatilization from dry soil may occur(SRC). 1,1-Dimethoxyethane's Henry's Law constant(1,SRC) indicates that volatilization from moist soil may also occur(SRC). |
| Non-Human Toxicity Excerpts | Irritant effects to rabbit: slight skin, moderate eye. /From table/Inhalation toxicity to rat: at 16,000 ppm for 4 hours the mortality was 3/6. /From table/ |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 1,1-dimethoxyethane with photochemically produced hydroxyl radicals has been experimentally determined to be 8.89X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 43 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2377 |
| Zollcode | 2911 00 00 |
| RTECS-Nr. | AB2825000 |
| R-Sätze (R) | 11 |
| Toxizität | LD50 orally in rats: 6.5 g/kgLC (in air) in rats: 16000 ppm (Smyth) |
| Gefahrensymbole | F |
| Sicherheitshinweise (S) | 9-16-33 |
| Gefahrenklasse | 3Flam. Liq. 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 534-15-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found in raspberry, blackberry, strawberry, peas, fresh figs, hop oil, coffee, cognac, white wine and tea.
Verwenden
1,1-Dimethoxyethane is used as a reagent in the synthesis of tricyclic and tetracyclic 1,5-benzodiazepine derivatives as nevirapine analogues. It can also be used as Mering's mixture which is 2 vol dimethylacetal and 1 vol chloroform.
Herstellung & Synthese
synthetische
From acetaldehyde and methanol.