出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/05 02:22:43」(JST)
| 1,2-Dibromoethane | |
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IUPAC name
1,2-Dibromoethane[1] |
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Other names
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| Identifiers | |
| Abbreviations | EDB[citation needed] |
| CAS number | 106-93-4 Y |
| PubChem | 7839 |
| ChemSpider | 7551 Y |
| EC number | 203-444-5 |
| UN number | 1605 |
| KEGG | C11088 Y |
| MeSH | Ethylene+Dibromide |
| ChEBI | CHEBI:28534 Y |
| ChEMBL | CHEMBL452370 Y |
| RTECS number | KH9275000 |
| Beilstein Reference | 605266 |
| Jmol-3D images | Image 1 |
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SMILES
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InChI
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| Properties | |
| Molecular formula | C2H4Br2 |
| Molar mass | 187.86 g mol−1 |
| Appearance | Colorless liquid |
| Density | 2.18 g mL−1 |
| Melting point |
9-10 °C, 282.5-283.3 K, 49-50 °F |
| Boiling point |
129-133 °C, 402-406 K, 264-271 °F |
| Vapor pressure | 1.56 kPa |
| kH | 14 μmol Pa kg−1 |
| Refractive index (nD) | 1.539 |
| Thermochemistry | |
| Std enthalpy of combustion ΔcH |
−1.2419–−1.2387 MJ mol−1 |
| Standard molar entropy S |
223.30 J K−1 mol−1 |
| Specific heat capacity, C | 134.7 J K−1 mol−1 |
| Hazards | |
| GHS pictograms | |
| GHS signal word | DANGER |
| GHS hazard statements | H301, H311, H315, H319, H331, H335, H350, H411 |
| GHS precautionary statements | P261, P273, P280, P301+310, P305+351+338 |
| EU Index | 602-010-00-6 |
| EU classification | T N |
| R-phrases | R45, R23/24/25, R36/37/38, R51/53 |
| S-phrases | S45 |
| NFPA 704 |
0
3
0
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| Flash point | >104 °C |
| LD50 |
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| Related compounds | |
| Related alkanes |
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| Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH2Br)2. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant.[2]
Contents
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It is produced by the reaction of ethylene with bromine, in a classic halogen addition reaction:
Historically, 1,2-dibromoethane was used as an anti-knock additive in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine.[3]
It has been used as a pesticide in soil and on various crops. The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP).[2] Most of these uses have been stopped in the U.S. It continues to be used as a fumigant for treatment of logs for termites and beetles, for control of moths in beehives.[4]
Ethylene bromide has wider applications in the preparation of other organic compounds. It is used to make vinyl bromide, a precursor to some fire retardants.[2]
In the laboratory, 1,2-dibromoethane is used in organic synthesis as a source of bromine, e.g., to brominate carbanions and to activate magnesium for certain Grignard reagents. In the latter process, the 1,2-dibromoethane is converted to ethylene and magnesium bromide, exposing a freshly etched portion of magnesium to the substrate.[5]
The effects 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. 1,2-Dibromoethane is not known to cause birth defects in humans.[6] Swallowing has caused death at 40 mL doses[4]
It is a known carcinogen, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index.[7]
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| リンク元 | 「二臭化エチレン」「エチレンジブロマイド」 |
| 関連記事 | 「ethylene」 |