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Allylbromid
3-BROMOPROPENE · 3-BROMO-1-PROPENE · 3-bromopropane · Allylbromid · 3-BROMOPROPYLENE · BROMALLYLENE · 3-Brompropen · 3-bromo-prop-1-ene
Identifikatoren & physikalische Daten
| CAS No. | 106-95-6 |
|---|---|
| Summenformel | C3H5Br |
| Durchschnittliche Molmasse | 120,98 g/mol |
| Monoisotopische Masse | 119,95746226 g/mol |
| SMILES | C=CCBr |
| InChIKey | BHELZAPQIKSEDF-UHFFFAOYSA-N |
| PubChem CID | 7841 |
| ChEMBL | CHEMBL1429506 |
| EC No. | 203-446-6 |
| DTXSID | DTXSID8024442 |
| Lokaler Name | Allylbromid |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 4 |
| Formalladung | 0 |
| Komplexität | 17,2 |
| Stoffklassen | Other Classes -> Halogenated Aliphatics, UnsaturatedFlammable agents - 3rd degree |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (Verteilungskoeffizient) | log Kow = 1.791.9 |
| Geruch | Unpleasant, pungent |
| Dichte | 1.4161 at 68 °F (USCG, 1999) - Denser than waterwill sink1.398 at 20 °C/4 °C1.3980 @ 20°C1.398 g/mL at 25 °C(lit.) |
| Color/Form | Colorless to light yellow liquid |
| Löslichkeit | Miscible with alcohol, chloroform, ether, carbon disulfide, carbon tetrachlorideIn water, 3,835 mg/L at 25 °CChloroform (Soluble)insoluble |
| Flammpunkt | 28 °F (USCG, 1999)-1 °C30 °F (-1 °C) |
| Siedepunkt | 158 °F at 760 mmHg (USCG, 1999)71.3 °C at 760 mm Hg71.3 °C @760 [mm Hg]70-71 °C(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen bromide/. |
| Schmelzpunkt | -182 °F (USCG, 1999)-119 °C |
| Dampfdichte | 4.17 (Air = 1)4.2 (vs air) |
| Dampfdruck | 18.66kPa at 25℃ |
| Brechungsindex | n20/D 1.469(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to slightly colored |
| Wichte | 1.398 |
| Geruch | unpleasant |
| Explosionsgrenze | 4.3-7.3%(V) |
| Merck | 14,288 |
| BRN | 605308 |
| Henry-Konstante | 1.7×10-3 mol/(m3Pa) at 25℃, Yaws (2003) |
| Dielektrizitätskonstante | 7.0 |
| Stabilität | Stable. Flammable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C3H5Br/c1-2-3-4/h2H,1,3H2 |
| InChIKey | BHELZAPQIKSEDF-UHFFFAOYSA-N |
| SMILES | BrCC=C |
| LogP (Verteilungskoeffizient) | 1.79 |
| CAS Datenbank | 106-95-6(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Propene, 3-bromo-(106-95-6) |
| EPA chemische Informationen | 3-Bromopropene (106-95-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (92.6%): Highly Flammable liquid and vapor [Danger Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P318, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 68 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: 1-Propene, 3-bromo-1-Propene, 3-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propene, 3-bromo- 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: 18-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/103333-Bromo-1-propene: HSNO Approval: HSR004256 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.) |
| DOT-Kennzeichnung | Flammable Liquid Poison |
| Brandgefahren | Special Hazards of Combustion Products: Toxic hydrogen bromide and bromine gases formed in fire.· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | Dangerous fire and explosion hazard when exposed to heat or flame. |
| Gesundheitsgefahren | Inhalation of vapor irritates mucous membranes and causes dizziness, headache, and lung irritation. Contact with liquid irritates eyes and skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| Gefahrenübersicht | A skin, eye, and respiratory tract irritantMay cause severe burns to skin and eyesMay be mutagenic[HSDB] May polymerizeA strong reducing agent[CAMEO] No evidence of carcinogenic activity in mice fed up to 8 mg/kg by corn oil gavage 5 days a week for 40 weeks[NTP] TLV basis is eye and upper respiratory tract irritant[ACGIH] A lachrymator[CHEMINFO] |
| DOT-Nummer und Handbuch | 1099 131P |
| Reaktive Gruppe | Halogenated Organic Compounds |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | ALLYL BROMIDE decomposes upon heating and exposure to light, forming HBr (a strong reducing agent). Reacts violently with oxidizing agents. Can react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. |
| Flammable Limits | Lower flammable limit: 4.4% by volumeUpper flammable limit: 7.3% by volume |
| DOT Emergency Guidelines | /GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ 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 and poison 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 131: FLAMMABLE LIQUIDS - TOXIC/ Health: TOXICmay be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will 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 131: FLAMMABLE LIQUIDS - TOXIC/ 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 131: FLAMMABLE LIQUIDS - TOXIC/ 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 ALLYL BROMIDE (8 total), please visit the HSDB record page. |
| Brandbekämpfung | Excerpt from ERG Guide 131 [Flammable Liquids - Toxicpolymerization 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 | INHALATION: remove from exposureif not breathing, give artificial respirationif breathing is difficult, give oxygencall physician.General First Aid: |
| Firefighting Hazards | Vapors are heavier than air and may travel to a source of ignition and flash back. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).257.0 [ppm] |
| Brandbekämpfungsverfahren | Water may be ineffective.Use dry chemical, foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomp products.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 spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius. |
| Lagerbedingungen | Separate from oxidizing materials, alkalies. Store in cool, dry, well-ventilated location.Keep tightly closed. |
| Reinigungsverfahren | Spill or leak procedures: Releases may require isolation or evacuation. Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and supress vapors. Absorb in noncombustible material for proper disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 131 [Flammable Liquids - Toxicpolymerization hazard]: |
| 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. |
| 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.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 disperse vapors and dilute standing pools of liquid.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 amounts 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.For more Preventive Measures (Complete) data for ALLYL BROMIDE (6 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 131 [Flammable Liquids - Toxicpolymerization hazard]:Immediate precautionary measure |
| 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. |
| Wechselwirkungen | In rats, cysteine magnesium nitrate and cysteine magnesium acetate administration ip resulted in 17-33% higher survival rate following allyl bromide poisoning than did cysteine administration. Cysteine magnesium bromide was as effective as cysteine against allyl bromide poisoning. |
| Gesundheitliche Auswirkungen | Acute poisoning of laboratory animals is accompanied by a transient motor agitation followed by depression and loss of balance. Death occurs within 24 hours. Allyl bromide is considered as one of the most toxic of the halogenated hydrocarbons, causing deaths in experimental animals exposed for 4 hr to concentrations as low as 1 mg/L. It is mutagenic but there is no evidence that it is carcinogenic. Target organs are gastrointestinal system, eyes, skin, respiratory system. |
| Ökotoxizitätswerte | LC50 Carassius auratus (Goldfish) <800 ug/L/24 hrstaticLC50 Xenopus laevis (Clawed toad) 660 ug/L/48 hrstatic /formulated product/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 230(SRC), determined from a log Kow of 1.79(2) and a regression-derived equation(3), indicates that allyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of allyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Allyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 140 mm Hg(SRC), determined from a fragment constant method(5). Based on BOD values of 56 and 74% in 5 days using sewage sludge(6), biodegradation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 230(SRC), determined from a log Kow of 1.79(2) and a regression-derived equation(3), indicates that allyl bromide 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 1.1X10-2 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 3 hours and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 5(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on BOD values of 56 and 74% in 5 days using sewage sludge(8), biodegradation may be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allyl bromide, which has an estimated vapor pressure of 140 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase allyl bromide 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 20 hours(SRC), calculated from its rate constant of 2.0X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). In addition, vapor-phase allyl bromide will react with ozone with a half-life of 7 days(SRC) calculated from an estimated rate constant of 1.5X10-16 cu cm/ molecule-sec(SRC), that was derived using a structure estimation method(3). Allyl bromide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | Oral (L626)inhalation (L626)dermal (L626) |
| Toxizitätsübersicht | Organobromide compounds such as allylbromide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Allyl bromide appears to target the stomach and lining of the stomach as animals given chronically high doses exhibit lesions of the forestomach, including hyperplasia, inflammation, degeneration, and hyperkeratosis. Alkylation of DNA by alkylbromides may also lead to mutations or a reduced ability of cells to divide. |
| Signs and Symptoms | Causes severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Causes gastrointestinal burns. |
| 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=106-95-6] |
| Soil Adsorption/Mobility | The Koc of allyl bromide is estimated as 230(SRC), using a log Kow of 1.79(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that allyl bromide is expected to have moderate mobility in soil. |
| TSCA Test Submissions | Toxicity of 3-bromopropene (BP) with respect to testicular changes was evaluated in male albino Wistar rats (10/treated group, 20 in arachis oil vehicle control group) exposed orally to BP by gavage at dosage levels of 15 or 60 mg/kg/day for 14 days. On day 15, the animals were sent for pathological examination. Significant differences between treated and control animals were observed only in reduced body weights (high-dose level). No significant differences between treated and control animals were observed in the following: testes weights, morphology, or detailed macroscopic and microscopic examination of the kidneys, testes, epididymides, ductuli efferentes, and vasa deferentes.3-Bromopropene (CAS # 106-95-6) was evaluated for subchronic oral toxicity. The test substance was administered by oral gavage to 10 male rats/group for 14 days at 15 mg/kg or 60 mg/kg. Additional groups were exposed to the control vehicles (water or arachis oil) or the positive control, glycerol-a-monochlorohydrin. At 60 mg/kg, signs of compound-related intoxication included excessive salivation in a small number of animals, severe gastric irritation, reduced body weights, and reduced body weight gains. Exposure caused no morphological changes of the reproductive tract and no significant changes in mean testes weights. |
| F | 8-19 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1099 |
| Zollcode | 29033036 |
| RTECS-Nr. | UC7090000 |
| R-Sätze (R) | 11-23/25-34-50-25-46-45 |
| Toxizität | LD50 orally in Rabbit: 120 mg/kg |
| Gefahrensymbole | F,T,N |
| Sicherheitshinweise (S) | 16-26-36/37/39-45-60-61-53 |
| Gefahrenklasse | 3Acute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Carc. 1BEye Dam. 1Flam. Liq. 2Muta. 1BSkin Corr. 1B |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 106-95-6(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 554 °F |
Anwendungen & Verwendung
Beschreibung
Das 3-Brom-1-propen bildet eine farblose, wasserunlösliche Flüssigkeit. Die Verbindung findet vielfältige Anwendung bei organischen Synthesen.