Bromoethane
|
| |||
|
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Bromoethane[2] | |||
| Other names | |||
| Identifiers | |||
3D model (JSmol)
|
|||
| 1209224 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). | ||
| EC Number |
| ||
| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). | ||
| KEGG | |||
| MeSH | bromoethane | ||
PubChem CID
|
|||
| RTECS number |
| ||
| UNII | |||
| UN number | 1891 | ||
CompTox Dashboard (EPA)
|
| ||
| |||
| Properties | |||
| C2H5Br | |||
| Molar mass | 108.966 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) | |||
| Solubility | miscible with ethanol, ether, chloroform, organic solvents | ||
| log P | 1.809 | ||
| Vapor pressure | 51.97 kPa (at 20 °C) | ||
Henry's law
constant (kH) |
1.3 μmol Pa−1 kg−1 | ||
| −54.70·10−6 cm3/mol | |||
Refractive index (nD)
|
1.4225 | ||
| Viscosity | 402 Pa.s (at 20 °C) | ||
| Thermochemistry | |||
Heat capacity (C)
|
105.8 J K−1 mol−1 | ||
Std enthalpy of
formation (ΔfH⦵298) |
−97.6–93.4 kJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
| GHS02: Flammable GHS06: Toxic GHS08: Health hazard | |||
| Danger | |||
| H225, H302, H332, H351 | |||
| P210, P281 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | −23 °C (−9 °F; 250 K) | ||
| 511 °C (952 °F; 784 K) | |||
| Explosive limits | 6.75–11.25% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
|
1.35 g kg−1 (oral, rat) | ||
LC50 (median concentration)
|
26,980 ppm (rat, 1 hr) 16,230 ppm (mouse, 1 hr) 4681 ppm (rat) 2723 ppm (mouse)[3] | ||
LCLo (lowest published)
|
3500 ppm (mouse) 24,000 ppm (guinea pig, 30 min) 7000 ppm (guinea pig, >4.5 hr)[3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
|
TWA 200 ppm (890 mg/m3)[1] | ||
REL (Recommended)
|
None established[1] | ||
IDLH (Immediate danger)
|
2000 ppm[1] | ||
| Related compounds | |||
Related alkanes
|
|||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |||
Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor.
Preparation
[edit | edit source]The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of hydrogen bromide 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.[4]
Uses
[edit | edit source]In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et+) synthon.[5] In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters,[6] carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts,[7] and amines into ethylamines.[8]
Safety
[edit | edit source]Short chain monohalocarbons in general are potentially dangerous alkylating agents. Bromides are better alkylating agents than chlorides, thus exposure to them should be minimized.
References
[edit | edit source]- ^ a b c d e Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).; Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).; Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).; Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).; Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).; Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
External links
[edit | edit source]- International Chemical Safety Card 1378
- NIOSH Pocket Guide to Chemical Hazards
- IARC Monograph: "Bromoethane"
Lua error in Module:Authority_control at line 153: attempt to index field 'wikibase' (a nil value).