HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-Brompropan
ISOPROPYL BROMIDE · 2-Brompropan · iso-C3H7Br · 2-BROMOPROPANE · 2-bromo-propan · bromo-2propane · propane,2-bromo- · bromo isopropane
Identifikatoren & physikalische Daten
| CAS No. | 75-26-3 |
|---|---|
| Summenformel | C3H7Br |
| Durchschnittliche Molmasse | 122,99 g/mol |
| Monoisotopische Masse | 121,97311232 g/mol |
| SMILES | CC(C)Br |
| InChIKey | NAMYKGVDVNBCFQ-UHFFFAOYSA-N |
| PubChem CID | 6358 |
| ChEMBL | CHEMBL451810 |
| EC No. | 200-855-1 |
| DTXSID | DTXSID7030197 |
| Lokaler Name | 2-Brompropan |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 4 |
| Formalladung | 0 |
| Komplexität | 10,8 |
| Stoffklassen | Flammable agents - 3rd degree |
| Solvents | Solvents -> Brominated Solvents |
| SpringerMaterials Properties | Coriolis coupling |
| LogP (Verteilungskoeffizient) | log Kow = 2.14 |
| Dichte | 1.31 at 20 °C/4 °C1.31 @ 20°C1.31 g/mL at 25 °C (lit.) |
| Viscosity | 1.0012X10-3 Pa.s (liquid) @ -23.15 °C |
| Color/Form | Colorless liquid |
| Löslichkeit | Miscible with alcohol, benzene, chloroform, etherSLIGHTLY SOL IN ACETONEIn water, 3,180 mg/L at 20 °C3.18g/l0.3 g/100 mL |
| Flammpunkt | 71.6 °F67 °F |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 59-60 °C138 °F59.35 °C @760 [mm Hg]59 °C (lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen bromide/. |
| Schmelzpunkt | -89 °C (lit.) |
| Dampfdruck | 224 hPa (20 °C) |
| Brechungsindex | n20/D 1.425(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to very light brown |
| Explosionsgrenze | 4.6%(V) |
| Merck | 14,5210 |
| BRN | 741852 |
| Henry-Konstante | 9.0×10-4 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 9.4600000000000009 |
| Stabilität | Stable. Flammable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C3H7Br/c1-3(2)4/h3H,1-2H3 |
| InChIKey | NAMYKGVDVNBCFQ-UHFFFAOYSA-N |
| SMILES | CC(C)Br |
| CAS Datenbank | 75-26-3(CAS DataBase Reference) |
| NIST chemische Informationen | Propane, 2-bromo-(75-26-3) |
| EPA chemische Informationen | Propane, 2-bromo- (75-26-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P280, P303+P361+P353, P318, P319, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 1.2% (1 of 85) of reports.H225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Propane, 2-bromo-Hazard Traits - CarcinogenicityDevelopmental ToxicityReproductive ToxicityPropane, 2-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-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: No longer Valid Update: 22-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1580Propane, 2-bromo-: 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 - Propane, 2-bromo-: Human health tier II assessment |
| Brandpotenzial | A very flammable liquid and dangerous fire hazard. |
| Gefahrenübersicht | In 1995, an outbreak was reported in Korean electronics workers using 2-BP to degrease switches. Adverse effects were amenorrhea and severe anemia in 17/25 females and oligospermia or azospermia in 6/8 males. The work area concentration was 12.4 ppm, and some workers had skin contact. In a Chinese plant manufacturing 2-BP, 25 workers were studied. Four females exposed at >10 ppm had amenorrhea or polymenorrhea. [ACGIH] See 1-Bromopropane. |
| DOT Emergency Guidelines | /GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ 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 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may 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 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ 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 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ 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 2-BROMOPROPANE (8 total), please visit the HSDB record page. |
| Hazard Classes and Categories | Flam. Liq. 2 (98.8%)Flammable liquid - category 2Flammable liquids - Category 2Flammable agents - 3rd degree |
| Shipment Methods and Regulations | No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. |
| Shipping Name/ Number DOT/UN/NA/IMO | UN 2344BromopropanesIMO 3.2 |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. /Bromopropanes/ |
| Lagerbedingungen | ...Materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well ventilated place, out of the direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected. Incompatible materials should be isolated... |
| 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 on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. /Bromopropanes/Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing. /Bromopropanes/ |
| Protective Action Criteria (PAC) | 3.0 [ppm]230 [ppm]1400 [ppm] |
| Personal Protective Equipment (PPE) | Personnel Protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Bromopropanes/ |
| 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 | 2-Bromopropane is a strong lachrymator. Chronic exposure has been shown to have teratogenic effects in mouse and rat embryos. Very high chronic doses led to developmental toxicity which included an increase in the fetal deaths, a decrease in the litter size, and a reduction in the fetal body weight. In addition, an increase in the incidence of fetal external, visceral, and skeletal abnormalities was seen. Chronic exposure to 2-bromopropane depletes spermatogenic cells in male rats and oocytes in female rats. Humans exposed to 2-bromopropane exhibited oligospermia, amenorrhea and other reproductive toxic effects. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow of 2.14(2) and a regression derived equation(3), indicates that isopropyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of isopropyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.011 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure of 216 mm Hg(4) and water solubility of 3180 mg/L(5). The potential for volatilization of isopropyl bromide from dry soil surfaces exists(SRC) based upon its extrapolated vapor pressure(4). No terrestrial biodegradation data were located for isopropyl bromide(SRC, 2005)however, an aqueous aerobic screening study using an activated sludge inoculum indicated that this compound is readily biodegradable(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow of 2.14(2) and a regression derived equation(3), indicates that isopropyl 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 0.011 atm-cu m/mole(SRC), derived from an extrapolated vapor pressure of 216 mm Hg(4) and water solubility of 3180 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 hour and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 9(SRC), from a log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The hydrolysis half-life of isopropyl bromide was reported as 2.1 days at 25 °C(8). No aquatic biodegradation data were located for isopropyl bromide(SRC, 2005)however, an aqueous aerobic screening study using an activated sludge inoculum indicated that this compound is readily biodegradable(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl bromide, which has an extrapolated vapor pressure of 216 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropyl 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 18 days(SRC), calculated from its rate constant of 8.8X10-13 cu cm/molecule-sec at 25 °C(3). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | Oral (L626)inhalation (L626)dermal (L626) |
| Toxizitätsübersicht | Organobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, 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. Alkylation of DNA by alkylbromides may also lead to mutations. 2-bromopropane triggers the mitochondrion-dependent apoptotic pathway via ROS (reactive oxygen species) generation. 2-bromopropane has also been shown to induce DNA damage, impair functional antioxidant cellular defenses, and enhance the lipid peroxidation in cultured Leydig cells. |
| Signs and Symptoms | May cause skin, eye and respiratory tract irritation. May affect behavior/central nervous system (central nervous system depression, excitement fatigue, headache, dizziness, stupor,unconsciousness and possible coma). If ingested, 2-bromopropane may cause gastrointestinal tract irritation with nausea, and vomiting. It may also affect behavior/central nervous system with symptoms similar to those for inhalation. May also cause kidney damage and liver damage. |
| Soil Adsorption/Mobility | The Koc of isopropyl bromide is estimated as 350(SRC), using a measured log Kow of 2.14(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that isopropyl bromide is expected to have moderate mobility in soil(SRC). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ An outbreak of reproductive and hematopoietic toxicities occurred in Korean electronics workers in 1995 exposed to solvents containing 2-BP that were used as alternatives to chlorofluorocarbons for cleaning tactile switches. Seventeen of 25 female workers showed ovarian dysfunction accompanied by amenorrhea and severe anemia, and 6 of 8 male workers had oligospermia or azospermia. The mean ambient 2-BP concentration in the work area was 12.4 ppm, and the 2-BP concentration inside the hood of the cleaning baths was 4141 ppm. Some workers had skin contact with 2-BP. Two of the affected female workers regained normal ovarian function within 2 years following exposure./HUMAN EXPOSURE STUDIES/ Sixteen Korean female laborers who had been exposed to a cleaning solvent composed mainly of 2-bromopropane developed primary ovarian failure. Histologic findings from these patients' ovaries were similar to those observed in ovarian failure caused by radiation or chemotherapy, i.e., reduced number and developmental arrest of primary follicles, interstitial fibrosis and hyalinization of blood vessels. We followed their clinical course for 2 years and found that two patients recovered normal ovarian function spontaneously: one became pregnant and delivered a normal full-term baby, and the other resumed regular menstrual periods with normal hormonal values. Our observations support the idea that the increasing prevalence of ovarian failure in recent years might be due to an increase in presently unidentified environmental toxic agents./HUMAN EXPOSURE STUDIES/ A study of 25 workers in a Chinese 2-BP manufacturing plant found amenorrhea or polymenorrhea in 4 female workers exposed at >10 ppm (TWA) 2-BP. |
| Artificial Pollution Sources | Isopropyl bromide's production and use in the synthesis of pharmaceuticals, dyes, and other organics(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | Isopropyl bromide present at 100 mg/L, reached 73-89% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). Half-lives for the biodehalogenation of isopropyl bromide are 35 (oxygen insertion), 279 (substitution), and 40 hours (substitution) by the bacterial strains Pseudomonas putida, Pseudomonas sp., and Flavobacterium sp., respectively(2). |
| Carcinogen Classification | 2-BromopropaneGroup 2A: Probably carcinogenic to humansVolume 133: (2024) Anthracene, 2-Bromopropane, Butyl Methacrylate, and Dimethyl Hydrogen Phosphite2024 online2023No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2344 3/PG 2 |
| Zollcode | 29033036 |
| RTECS-Nr. | TX4111000 |
| R-Sätze (R) | 60-11-48/20-66 |
| Gefahrensymbole | F,T |
| Sicherheitshinweise (S) | 53-16-45 |
| Gefahrenklasse | 3Flam. Liq. 2Repr. 1ASTOT RE 2 Inhalation |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 75-26-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula CH3CHBrCH3. It is a colorless liquid. It is used for introducing the isopropyl functional group in organic synthesis. 2-Bromopropane is prepared by heating isopropanol with hydrobromic acid.
Verwenden
2-Bromopropane is a general reagent used to introduce isopropyl group as in the case of the synthesis of various Buchwald ligands. It can also be used as a starting material in the total synthesis of lamellarin D, lamellarin H, ningalin B and (±)-dichroanal. It is sometimes used as an alternative to ozone-depleting cleaning solvents such as chlorofluorocarbons.
Herstellung & Synthese
synthetische
2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine, or with phosphorus tribromide.