HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1-Brom-2-phenylethan
PHENETHYL BROMIDE · 2-PHENYLETHYL BROMIDE · 2-Phenethyl bromide · Benzene, (2-bromoethyl)- · 1-BROMO-2-PHENYLETHANE · PHENYL ETHYL BROMIDE · β-BroMoethyl-benzene · 1-phenyl-2-bromoethane
Identifikatoren & physikalische Daten
| CAS No. | 103-63-9 |
|---|---|
| Summenformel | C8H9Br |
| Durchschnittliche Molmasse | 185,06 g/mol |
| Monoisotopische Masse | 183,98876239 g/mol |
| SMILES | BrCCc1ccccc1 |
| InChIKey | WMPPDTMATNBGJN-UHFFFAOYSA-N |
| PubChem CID | 7666 |
| ChEMBL | CHEMBL1340745 |
| EC No. | 203-130-8 |
| DTXSID | DTXSID1033876 |
| Lokaler Name | 1-Brom-2-phenylethan |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 65 |
| Stoffklassen | Other Classes -> Halogenated Monoaromatics |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | Log Kow = 3.09 |
| Dichte | Density = 1.3551.355 g/mL at 25 °C(lit.) |
| Löslichkeit | Sol in ether, benzeneslightly soluble in carbon tetrachlorideWater solubility = 39.05 mg/l at 25 °C0.039g/lINSOLUBLE |
| Siedepunkt | 219 °C220-221 °C(lit.) |
| Schmelzpunkt | -67.5 °C-56 °C |
| Dampfdruck | 0.24 [mmHg]Vapor pressure = 0.2445 mm Hg at 25 °C |
| Brechungsindex | INDEX OF REFRACTION: 1.5572 AT 20 °CSADTLER REFERENCE NUMBER: 4682 (IR, PRISM), 434 (IR, GRATING)n20/D 1.556(lit.) |
| Physical Description | LiquidColorless liquid[MSDSonline] |
| Flammpunkt | 193 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to pale yellow |
| BRN | 507487 |
| Henry-Konstante | 6.5×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2 |
| InChIKey | WMPPDTMATNBGJN-UHFFFAOYSA-N |
| SMILES | BrCCc1ccccc1 |
| CAS Datenbank | 103-63-9(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Bromo-2-phenylethane(103-63-9) |
| EPA chemische Informationen | Benzene, (2-bromoethyl)- (103-63-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 88 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, (2-bromoethyl)-Benzene, (2-bromoethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, (2-bromoethyl)- 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: 04-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/196732-Phenylethyl bromide: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes somnolence in lethal-dose feeding studies of rats[RTECS] Effects observed in rats that died during seven day feeding study include reddened adrenal glands, hemorrhagic thymus glands, and intestinal abnormalities[HSDB] An irritant[MSDSonline] See Benzyl bromide. |
| Hazard Classes and Categories | Acute Tox. 4 (98.9%)Flammable liquids - Category 4 |
| 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. |
| Umweltverhalten | TERRESTRIAL FATE: (2-Bromoethyl)benzene will have low mobility(3) in soil based on estimated Koc values of 581.6 and 955(1,2,SRC). Insufficient data are available to determine the rate or importance of biodegradation of (2-bromoethyl)benzene in soil conditions. Volatilization of (2-bromoethyl)benzene is expected from moist and dry soils based on an experimental vapor pressure of 0.2445 mm Hg at 25 °C(4) and an Henry's Law constant of 1.52X10-3 atm cu m/mole estimated from an experimental water solubility of 39.05 mg/l(4) and a vapor pressure of 0.2445 mm Hg(4).AQUATIC FATE: (2-Bromoethyl)benzene is expected to volatilize rapidly from water(1) based upon an estimated Henry's Law constant of 1.52X10-3 atm cu m/mol estimated from an experimental water solubility of 39.05 mg/L(2) and a vapor pressure of 0.2445 mm Hg(2). Based on this Henry's Law constant the volatilization half-life from a model river (1 meter deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 4.8 hours(1,SRC). The volatilization half-life from a model lake (1 meter deep) can be estimated to be about 5.6 days(1,SRC). Insufficient data are available to determine the rate or importance of biodegradation of (2-bromoethyl)benzene in aquatic conditions(SRC). Aquatic bioconcentration and adsorption to sediment may be important fate processes in aquatic systems based on an estimated BCF of 78(1,SRC) and estimated Koc values of 582 and 955(1,3,SRC) but hydrolysis is not expected to be important(SRC).ATMOSPHERIC FATE: Based on an experimental vapor pressure of 0.2445 mm Hg at 25 °C(1), (2-bromoethyl)benzene will exist in the atmosphere in the vapor phase(2). It will degrade in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of 2.87 days(3). Removal of (2-bromoethyl)benzene from the atmosphere can occur through wet deposition(SRC). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices, the Koc for (2-bromoethyl)benzene can be estimated to be about 955(1). The Koc for (2-bromoethyl)benzene can also be estimated to be about 582 based on an experimental water solubility of 39.05 mg/l(3) and a regression derived equation(2). According to a suggested classification scheme(4), these estimated Koc values suggest that (2-bromoethyl)benzene has low soil mobility. |
| TSCA Test Submissions | 2-Bromoethylbenzene (CAS # 103-62-9) was evaluated for acute oral toxicity. The test substance was administered once orally, by gavage to groups of male and female fasted albino rats. Dosage and mortality data are as follows: 521 mg/kg (0/5 M, 0/5 F)750 mg/kg (2/5 M, 2/5 F)and 1080 mg/kg (5/5 M, 4/5 F). All deaths occurred within 7 days of dosing. The combined LD50 value was determined to be 811 mg/kg. At 521 mg/kg and above, treatment-related toxicity included hypoactivity and salivationat 750 mg/kg and above, ataxia, clear ocular discharge and labored breathing were seen. There also was a low incidence of urogenital staining, abnormal defecation, dry brown staining around nose, hypothermia, dried red material around the eye(s), prostration and rales. There were no treatment-related changes in body weights. Necropsy of rats that died revealed external matting, dark red or reddened adrenal glands, stomach abnormalities, hemorrhagic thymus glands, and intestinal abnormalities. |
| Artificial Pollution Sources | (2-Bromoethyl)benzene's use as a starting material for the production of various beta-phenethyl derivatives, pharmaceuticals, fragrances, and other fine chemicals(1) could result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | Based upon an experimental water solubility of 39.05 mg/l(1), the BCF of (2-bromoethyl)benzene can be estimated to be approximately 78 from a regression-derived equation(2). This estimated BCF value suggests that bioconcentration in aquatic organisms may be an important fate process(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for (2-bromoethyl)benzene can be estimated to be 1.52X10-3 atm-cu m/mole based on an experimental water solubility of 39.05(1) and an experimental vapor pressure of 0.2445(1). This value of the Henry's Law constant indicates that volatilization of (2-bromoethyl)benzene from water is rapid(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 meter deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 4.8 hours(2,SRC). The volatilization half-life from a model lake (1 meter deep) can be estimated to be about 5.6 days(2,SRC). |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of (2- bromoethyl)benzene with photochemically produced hydroxyl radicals has been estimated to be approximately 5.59X10-12 cu cm/molecule-sec at 25 °C, which corresponds to an atmospheric half-life of about 2.9 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). |
| Probable Routes of Human Exposure | Occupational exposure to bromine and compounds, such as (2-bromoethyl)benzene(SRC), can occur through dermal contact, inhalation, and ingestion(1). |
| Environmental Fate/Exposure Summary | (2-Bromoethyl)benzene's use as an starting material for the production of various beta-phenethyl derivatives, pharmaceuticals, and fragrances could result in its release to the environment through various waste streams. (2-Bromoethyl)benzene should have low mobility in soil. Volatilization of (2-bromoethyl)benzene is expected from both moist and dry soils. In water, (2-bromoethyl)benzene is expected to volatilize rapidly with estimated half-lives of 4.8 hours and 5.6 days from a model river and a model lake, respectively. Bioconcentration and adsorption to sediment may be important fate processes in aquatic systems, but hydrolysis is not expected to be important. Insufficient data are available to determine the rate or importance of biodegradation of (2-bromoethyl)benzene in either soil or aquatic conditions. (2-Bromoethyl)benzene will exist in the vapor phase in the ambient atmosphere. If released to the atmosphere, it will degrade by reaction with photochemically produced hydroxyl radicals with an estimated half-life of approximately 2.9 days. Removal of (2-bromoethyl)benzene from the atmosphere can occur through wet deposition. Exposure to (2-bromoethyl)benzene can occur through dermal contact, inhalation, and ingestion. (SRC) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1993 / PGIII |
| Zollcode | 29036990 |
| RTECS-Nr. | CY9032000 |
| R-Sätze (R) | 22-36-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-37/39-39 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 103-63-9(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralEye Irrit. 2 |
Anwendungen & Verwendung
Beschreibung
Phenethylbromide is an analytical reference material that is structurally categorized as an organobromide. It is used in the synthesis of a variety of compounds, including fentanyl. Phenethylbromide is combined with 4-piperidinone to produce N-phenethyl-4-piperidone, which, as a precursor in the synthesis of fentanyl, is scheduled as a List I chemical in the United States. Phenethylbromide may be found as in impurity in samples of fentanyl produced using this pathway.
Verwenden
(2-Bromoethyl)benzene is used in the preparation of phenelzine by reacting with hydrazine. It is also used as a starting material to prepare various beta-phenethyl derivatives, active pharmaceutical ingredients, and fragrances. It finds application as a flame retardant.
Verwenden
(2-Bromoethyl)benzene is an important starting material for the production of various b-phenethyl derivatives, pharmaceuticals, fragrances, and other fine chemicals.
Herstellung & Synthese
synthetische
(2-Bromoethyl)benzene is synthesized by the reaction of phenethyl alcohol with hydrogen bromide.Reaction: The phenethyl alcohol was heated to 110°C, hydrogen bromide was slowly introduced, and the reaction was refluxed. The reaction was completed, cooled, washed with water, 10% sodium carbonate solution, and water in turn. After drying with anhydrous potassium carbonate, fractional distillation under reduced pressure was carried out to collect fractions at 97-99°C (2.0 kPa) with a yield of over 90%.