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 | |
| Names | |
|---|---|
| Preferred IUPAC name 1-Bromobutane[1] | |
| Other names Butyl bromide | |
| Identifiers | |
| |
3D model (JSmol) | |
| 1098260 | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.003.357 |
| EC Number |
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| MeSH | butyl+bromide |
| RTECS number |
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| UNII | |
| UN number | 1126 |
| |
| |
| Properties | |
| C4H9Br | |
| Molar mass | 137.020 g·mol−1 |
| Appearance | Colourless liquid |
| Density | 1.2676 g mL−1 |
| Melting point | −112.5 °C; −170.4 °F; 160.7 K |
| Boiling point | 101.4 to 102.9 °C; 214.4 to 217.1 °F; 374.5 to 376.0 K |
| logP | 2.828 |
| Vapor pressure | 5.3 kPa |
Henry's law constant (kH) | 140 nmol Pa kg−1 |
Refractive index (nD) | 1.439 |
| Thermochemistry | |
| 162.2 J K−1 mol−1 | |
Std molar entropy(S⦵298) | 327.02 J K−1 mol−1 |
Std enthalpy of formation(ΔfH⦵298) | −148 kJ mol−1 |
Std enthalpy of combustion(ΔcH⦵298) | −2.7178–−2.7152 MJ mol−1 |
| Hazards | |
| GHS labelling: | |
   | |
| Danger | |
| H225,H315,H319,H335,H411 | |
| P210,P261,P273,P305+P351+P338 | |
| Flash point | 10 °C (50 °F; 283 K) |
| 265 °C (509 °F; 538 K) | |
| Explosive limits | 2.8–6.6% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 2.761 g kg−1(oral, rat) |
| Related compounds | |
Related alkanes | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Bromobutane is theorganobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble inorganic solvents. It is primarily used as a source of the butyl group inorganic synthesis. It is one of several isomers of butyl bromide.
Most 1-bromoalkanes are prepared by free-radical addition ofhydrogen bromide to the1-alkene. These conditions lead to the anti-Markovnikov addition, i.e. give the 1-bromo derivatives.[2]
1-Bromobutane can also be prepared frombutanol by treatment withhydrobromic acid:[3]
As a primaryhaloalkane, it is prone toSN2 type reactions. It is commonly used as analkylating agent. When combined withmagnesium metal in dryether, it gives the correspondingGrignard reagent. Such reagents are used to attach butyl groups to various substrates.
1-Bromobutane is the precursor ton-butyllithium:[4]
The lithium for this reaction contains 1-3% sodium. When bromobutane is the precursor, the product is a homogeneous solution, consisting of a mixed cluster containing both LiBr and LiBu.
1-Fluorobutane can be obtained by reacting 1-bromobutane withpotassium fluoride inethylene glycol.[5]
