Chemistry:1-Bromobutane
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| Names | |
|---|---|
| Preferred IUPAC name
1-Bromobutane[1] | |
| Other names
Butyl bromide
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| Identifiers | |
3D model (JSmol)
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| 1098260 | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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| MeSH | butyl+bromide |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1126 |
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| 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 |
| log P | 2.828 |
| Vapor pressure | 5.3 kPa |
Henry's law
constant (kH) |
140 nmol Pa kg−1 |
Refractive index (nD)
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1.439 |
| Thermochemistry | |
Heat capacity (C)
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162.2 J K−1 mol−1 |
Std molar
entropy (S |
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 pictograms |   
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| GHS Signal word | DANGER |
| H225, H315, H319, H335, H411 | |
| P210, P261, P273, P305+351+338 | |
| 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)
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2.761 g kg−1 (oral, rat) |
| Related compounds | |
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). | |
 verify (what is   ?)
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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 primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.
Synthesis
Most 1-bromoalkanes are prepared by free-radical addition of hydrogen bromide to the 1-alkene. These conditions lead to the anti-Markovnikov addition, i.e. give the 1-bromo derivatives.[2]
1-Bromobutane can also be prepared from butanol by treatment with hydrobromic acid:[3]
- 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, it gives the corresponding Grignard reagent. Such reagents are used to attach butyl groups to various substrates.
1-Bromobutane is the precursor to n-butyllithium:[4]
- 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
- ↑ "butyl bromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8002. Retrieved 17 June 2012.
- ↑ Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C.. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.
- ↑ 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
- ↑ Brandsma, L.; Verkraijsse, H. D. (1987). Preparative Polar Organometallic Chemistry I. Berlin: Springer-Verlag. ISBN 3-540-16916-4.
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