1-Bromobutane
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| Names | |
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| IUPAC name
1-Bromobutane[1]
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| Other names
Butyl bromide
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| Identifiers | |
109-65-9  |
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| 1098260 | |
| ChEMBL | ChEMBL160949 |
| ChemSpider | 7711 |
| EC Number | 203-691-9 |
| Jmol 3D model | Interactive image |
| MeSH | butyl+bromide |
| PubChem | 8002 |
| RTECS number | EJ6225000 |
| UN number | 1126 |
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| Properties | |
| C4H9Br | |
| Molar mass | 137.02 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 |
| log P | 2.828 |
| Vapor pressure | 5.3 kPa |
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Henry's law
constant (kH) |
140 nmol Pa kg−1 |
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Refractive index (nD)
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1.439 |
| Thermochemistry | |
| 162.2 J K−1 mol−1 | |
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Std molar
entropy (S |
327.02 J K−1 mol−1 |
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Std enthalpy of
formation (ΔfH |
−148 kJ mol−1 |
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Std enthalpy of
combustion (ΔcH |
−2.7178–−2.7152 MJ 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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| Infobox references | |
1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is a primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.
Synthesis
It is prepared from butanol by treatment with hydrobromic acid]]:[2]
- CH3(CH2)3OH + HBr → CH3(CH2)3Br + H2O
Reactions
As a primary haloalkane, it is prone to SN2 type reactions. It is commonly used as an alkylating agent. When combined with magnesium metal in dry ether is gives the corresponding Grignard reagent. Such reagents are used to attach butyl groups to various substrates.
1-Bromobutane is the precursor to n-butyllithium:[3]
- 2 Li + C4H9X → C4H9Li + LiX
- where X = Cl, Br
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.
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Oliver Kamm, C. S. Marvel, R. H. Goshorn, Thomas Boyd, And E. F. Degering "Alkyl And Alkylene Bromides" Org. Synth. 1921, volume 1, p. 3. doi:10.15227/orgsyn.001.0003
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
