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| Names | |||
|---|---|---|---|
| Preferred IUPAC name 1,2-Dibromoethane[1] | |||
| Other names | |||
| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | EDB[citation needed] | ||
| 605266 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.003.132 | ||
| EC Number |
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| KEGG |
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| MeSH | Ethylene+Dibromide | ||
| RTECS number |
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| UNII | |||
| UN number | 1605 | ||
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| Properties | |||
| C2H4Br2 | |||
| Molar mass | 187.862 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | faintly sweet[2] | ||
| Density | 2.18 g mL−1 | ||
| Melting point | 9.4 to 10.2 °C; 48.8 to 50.3 °F; 282.5 to 283.3 K | ||
| Boiling point | 129 to 133 °C; 264 to 271 °F; 402 to 406 K | ||
| 0.4% (20 °C)[2] | |||
| logP | 2.024 | ||
| Vapor pressure | 1.56 kPa | ||
Henry's law constant (kH) | 14 μmol Pa kg−1 | ||
Refractive index (nD) | 1.539 | ||
| Thermochemistry | |||
| 134.7 J K−1 mol−1 | |||
Std molar entropy(S⦵298) | 223.30 J K−1 mol−1 | ||
Std enthalpy of combustion(ΔcH⦵298) | −1.2419–−1.2387 MJ mol−1 | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | carcinogen[2] | ||
| GHS labelling: | |||
   | |||
| Danger | |||
| H301,H311,H315,H319,H331,H335,H350,H411 | |||
| P261,P273,P280,P301+P310,P305+P351+P338 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 104 °C (219 °F; 377 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
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LC50 (median concentration) | 1831 ppm (rat, 30 min) 691 ppm (rat, 1 hr)[3] | ||
LCLo (lowest published) | 200 ppm (rat, 8 hr) 400 ppm (guinea pig, 3 hr)[3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 20 ppm C 30 ppm 50 ppm [5-minute maximum peak][2] | ||
REL (Recommended) | Ca TWA 0.045 ppm C 0.13 ppm [15-minute][2] | ||
IDLH (Immediate danger) | Ca [100 ppm][2] | ||
| Related compounds | |||
Related alkanes | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
1,2-Dibromoethane, also known asethylene dibromide (EDB), is anorganobromine compound with thechemical formulaC
2H
4Br
2. Although trace amounts occur naturally in theocean, where it is probably formed byalgae andkelp, substantial amounts are produced industrially. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm. It is a widely used and sometimes-controversialfumigant.[4] The combustion of 1,2-dibromoethane produceshydrogen bromide gas that is significantly corrosive.[5]
It is produced by the reaction ofethylene gas withbromine,[6] in a classichalogen addition reaction:
Historically, 1,2-dibromoethane was used as a component in anti-knockadditives in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine with lead deposits.[7]
It has been used as apesticide insoil and on various crops. The applications were initiated after the forced retirement of1,2-dibromo-3-chloropropane (DBCP).[4] Most of these uses have been stopped in the U.S. It continues to be used as afumigant for treatment of logs fortermites andbeetles, and for control ofmoths inbeehives.[8]
1,2-Dibromoethane has wider applications in the preparation of other organic compounds including those carrying modified diazocine rings[9] and vinyl bromide that is a precursor to somefire retardants.[4]
Inorganic synthesis, 1,2-dibromoethane is used to brominatecarbanions and to activatemagnesium for certainGrignard reagents. In the latter process, 1,2-dibromoethane reacts with magnesium, producingethylene andmagnesium bromide, which are innocuous, exposing a more active portion of the magnesium particle to the substrate.[10]
1,2-Dibromoethane causes changes in themetabolism and severe destruction of living tissues.[5] The known empirical LD50 values for 1,2-dibromoethane are 140 mg kg−1 (oral, rat), and 300.0 mg kg−1 (dermal, rabbit).[5] 1,2-Dibromoethane is a knowncarcinogen, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index.[11]
Theeffects on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain. Changes in the brain and behavior were also seen in young rats whose male parents had breathed 1,2-dibromoethane, and birth defects were observed in the young of animals that were exposed while pregnant.[12] 1,2-Dibromoethane is not known to causebirth defects in humans. Swallowing has caused death at 40ml doses.[8]
