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Ethyl-bromacetat
ETHYL 2-BROMOACETATE · BROMOACETIC ACID ETHYL ESTER · ethylbromacetate · Ethyl-bromacetat · Antol · Bromoester · MethylBromate · hyl bromoacetate
Identifikatoren & physikalische Daten
| CAS No. | 105-36-2 |
|---|---|
| Summenformel | C4H7BrO2 |
| Durchschnittliche Molmasse | 167 g/mol |
| Monoisotopische Masse | 165,96294156 g/mol |
| SMILES | CCOC(=O)CBr |
| InChIKey | PQJJJMRNHATNKG-UHFFFAOYSA-N |
| PubChem CID | 7748 |
| ChEMBL | CHEMBL1085948 |
| EC No. | 203-290-9 |
| DTXSID | DTXSID4020587 |
| Lokaler Name | Ethyl-bromacetat |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 62,7 |
| Stoffklassen | Other Classes -> Halogenated EstersFlammable agents - 2nd degree |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| LogP (Verteilungskoeffizient) | log Kow= 1.12 |
| Geruch | Pungent odor |
| Dichte | 1.5032 @ 20 °C/20 °C1.5032 @ 20°C1.506 g/mL at 25 °C(lit.) |
| Color/Form | Clear colorless liquid |
| Löslichkeit | Insoluble in water, soluble in acetone, miscible in ethanol and ethyl ether.Sol in benzene and alcoholMiscible in oxygenated and aromatic solventswater: insolubleMiscible with ethanol, acetone, benzene and ethyl ether. Immiscible with water. |
| Flammpunkt | 48 °C118 °F (48 °C) (CLOSED CUP) |
| Siedepunkt | 168.5 °C158.8 °C @760 [mm Hg]159 °C(lit.) |
| Decomposition | When heated to decomposition ... it emits highly toxic fumes of /hydrogen bromide/. |
| Dampfdichte | 5.8 (Air= 1)5.8 (vs air) |
| Dampfdruck | 3.37 [mmHg]2.6 [mm Hg] @25 °C2.6 mm Hg ( 25 °C) |
| Schmelzpunkt | -38 °C |
| Brechungsindex | n20/D 1.451(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear |
| Wichte | 1.506 |
| Geruch | Pungent odour |
| BRN | 506456 |
| Henry-Konstante | 3.7×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielektrizitätskonstante | 9.75 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, water, strong acids. |
| InChI | 1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
| InChIKey | PQJJJMRNHATNKG-UHFFFAOYSA-N |
| SMILES | BrCC(=O)OCC |
| CAS Datenbank | 105-36-2(CAS DataBase Reference) |
| NIST chemische Informationen | Acetic acid, bromo-, ethyl ester(105-36-2) |
| EPA chemische Informationen | Acetic acid, 2-bromo-, ethyl ester (105-36-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.6% (1 of 164) of reports.H226 (93.3%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, bromo-, ethyl esterStatus: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18025Restricted substance: Ethyl bromoacetateEthyl bromoacetate: HSNO Approval: HSR004469 Approved with controlsThe 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 - Acetic acid, bromo-, ethyl ester: Human health tier I assessment |
| DOT-Kennzeichnung | Poison Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | Flammable liquid when exposed to heat, flame, and oxidizers. |
| Gesundheitsgefahren | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| Gefahrenübersicht | A skin, eye, and mucous membrane irritantContact with liquid can cause corneal burns[HSDB] A lachrymator and a strong skin irritant[CAMEO] Highly toxic[Quick CPC] A lachrymator--exposure to 8 ppm for more than 1 minute is unbearable[CHEMINFO] Inhalation of high concentrations may produce acute pneumonitis and pulmonary edema[MSDSonline] See Ethyl chloroacetate. |
| DOT-Nummer und Handbuch | 1603 155 |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | TOXICOLOGICAL ASPECTS OF IRRITATING AGENTS ETHYLBROMOACETATE. A REVIEW.[HOLMBERG BBIOLOGICAL ASPECTS OF CHEMICAL & BIOLOGICAL WEAPONSAMBIO 4(5-6) 211 (1975)] |
| Reactivity Profile | ETHYL BROMOACETATE is a halogenated 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 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water./GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Health: TOXICinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution./GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ 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 in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas./GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ 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 ONLYit is not effective in spill situations where direct contact with the substance is possible.For more DOT Emergency Guidelines (Complete) data for ETHYL 2-BROMOACETATE (8 total), please visit the HSDB record page. |
| Brandbekämpfung | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: |
| 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 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | To fight fire, use water as a fire blanket. |
| Freisetung ohne Brand | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: |
| 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 | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:Immediate precautionary measure |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: |
| Emergency Response Planning Guidelines | · Note: Most foams will react with the material and release corrosive/toxic gases. |
| Treatment | EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
| Gesundheitliche Auswirkungen | Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627) |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 1.12(2) and a regression-derived equation(3), indicates that ethyl 2-bromoacetate is expected to have very high mobility in soil(SRC). Volatilization of ethyl 2-bromoacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.70X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of ethyl 2-bromoacetate from dry soil surfaces may exist based upon an estimated vapor pressure of 3.37 mm Hg(5). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(6)this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 1.12(2) and a regression-derived equation(3), indicates that ethyl 2-bromoacetate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.70X10-5 atm-cu m/mole(SRC), developed using a fragment constant 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 17 hr and 12 days, respectively(SRC). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(7)this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(7). According to a classification scheme(5), an estimated BCF of 1(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl 2-bromoacetate, which has an estimated vapor pressure of 3.37 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl 2-bromoacetate 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 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | Oral (L626)inhalation (L626)dermal (L626) |
| Toxizitätsübersicht | Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543) |
| Signs and Symptoms | Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627) |
| Soil Adsorption/Mobility | The Koc of ethyl 2-bromoacetate is estimated as 12(SRC), using a log Kow of 1.12(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethyl 2-bromoacetate is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | VAPORS ARE IRRITANT TO ALL MUCOUS MEMBRANES, ESP TO EYES, & ARE UNBEARABLE FOR MORE THAN A MIN AT CONCN OF 8 PPM IN AIR. EXPOSURE OF HUMAN EYES TO HIGH CONCN OF VAPOR FROM TEAR GAS SHELLS HAS CAUSED CORNEAL EDEMA WITH WRINKLING OF DESCEMET'S MEMBRANE, BUT IN MOST PATIENTS THE EYES...RETURNED TO NORMAL.DIRECT CONTACT WITH LIQUID...HAS CAUSED PERMANENT CORNEAL SCARRING & OPACIFICATION.TOXIC BY INGESTION, INHALATION, & SKIN ABSORPTION. |
| Artificial Pollution Sources | Ethyl 2-bromoacetate's production and use as a chemical intermediate and reactant in the synthesis of an analgesic(1) may result in its release to the environment through various waste streams. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Environmental Bioconcentration | An estimated BCF of 1 was calculated for ethyl 2-bromoacetate(SRC), using a log Kow of 1.12(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. |
| F | 19 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1603 |
| Zollcode | 29159080 |
| RTECS-Nr. | AF6000000 |
| R-Sätze (R) | 26/27/28 |
| Gefahrensymbole | T+ |
| Sicherheitshinweise (S) | 26-45-7/9-1/2 |
| Gefahrenklasse | 6.1Acute Tox. 1 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralFlam. Liq. 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 105-36-2(Hazardous Substances Data) |
Herstellung & Synthese
synthetische
Ethyl bromoacetate is commonly synthesized by sulfuric acid catalyzed esterification of monobromoacetic acid (MBAA). After reaction completion, excess acid is washed out and the product purified via distillation under reduced pressure if necessary (Stenger, 1978; Korhonen, 1984).