Bromoethane
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| Names | |||
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| IUPAC name
Bromoethane[2]
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| Other names | |||
| Identifiers | |||
74-96-4  |
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| 1209224 | |||
| ChEMBL | ChEMBL156378 |
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| ChemSpider | 6092 |
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| EC Number | 200-825-8 | ||
| Jmol 3D model | Interactive image | ||
| KEGG | C19354  |
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| MeSH | bromoethane | ||
| PubChem | 6332 | ||
| RTECS number | KH6475000 | ||
| UN number | 1891 | ||
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| Properties | |||
| C2H5Br | |||
| Molar mass | 108.97 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | ether-like | ||
| Density | 1.46 g mL−1 | ||
| Melting point | −120 to −116 °C; −184 to −177 °F; 153 to 157 K | ||
| Boiling point | 38.0 to 38.8 °C; 100.3 to 101.8 °F; 311.1 to 311.9 K | ||
| 1.067 g/100 mL (0 °C) 0.914 g/100 mL (20 °C) 0.896 g/100 mL (30 °C) |
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| Solubility | miscible with ethanol, ether, chloroform, organic solvents | ||
| log P | 1.809 | ||
| Vapor pressure | 51.97 kPa (at 20 °C) | ||
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Henry's law
constant (kH) |
1.3 μmol Pa−1 kg−1 | ||
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Refractive index (nD)
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1.4225 | ||
| Viscosity | 402 Pa s (at 20 °C) | ||
| Thermochemistry | |||
| 105.8 J K−1 mol−1 | |||
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Std enthalpy of
formation (ΔfH |
−97.6–93.4 kJ mol−1 | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related alkanes
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |||
Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour.
Preparation
The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of HBr to ethene:
- H2C=CH2 + HBr → H3C-CH2Br
Bromoethane is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis includes reacting ethanol with a mixture of hydrobromic and sulfuric acids. An alternate route involves refluxing ethanol with phosphorus and bromine; phosphorus tribromide is generated in situ.[3]
Uses
In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et+) synthon.[4] In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters,[5] carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts,[6] and amines into ethylamines.[7]
Safety
Halocarbons in general are potentially dangerous alkylating agents. Bromides are better alkylating agents than chlorides, thus exposure to EtBr should be minimized. EtBr is classified by the State of California as carcinogenic and a reproductive toxin.
References
- ↑ 1.0 1.1 Cite error: Invalid
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