1-Bromobutane
| 1-Bromobutane | |
|---|---|
 | |
 | |
| 1-Bromobutane[1] | |
| Other names Butyl bromide[citation needed] | |
| Identifiers | |
| CAS number | 109-65-9  |
| PubChem | 8002 |
| ChemSpider | 7711 |
| EC number | 203-691-9 |
| UN number | 1126 |
| MeSH | butyl+bromide |
| ChEMBL | CHEMBL160949 |
| RTECS number | EJ6225000 |
| Beilstein Reference | 1098260 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | 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 | 99 to 103 °C; 210 to 217 °F; 372 to 376 K |
| log P | 2.828 |
| Vapor pressure | 5.3 kPa |
| kH | 140 nmol Pa kg−1 |
| Refractive index (nD) | 1.439 |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−148 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−2.7178–−2.7152 MJ mol−1 |
| Standard molar entropy S |
327.02 J K−1 mol−1 |
| Specific heat capacity, C | 162.2 J K−1 mol−1 |
| Hazards | |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H315, H319, H335, H411 |
| GHS precautionary statements | P210, P261, P273, P305+351+338 |
| EU classification |  F  Xi  N |
| R-phrases | R11, R36/37/38, R51/53 |
| S-phrases | S16, S26 |
| Flash point | 10 °C; 50 °F; 283 K |
| Autoignition temperature | 265 °C; 509 °F; 538 K |
| Explosive limits | 2.8–6.6% |
| LD50 | 2.761 g kg−1 (oral, rat) |
| Related compounds | |
| Related alkanes | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
1-Bromobutane (CH3(CH2)3Br) is a colorless liquid that is insoluble in water, but soluble in ethanol and diethyl ether. As a primary haloalkane, it is especially prone to SN2 type reactions. It is commonly used as an alkylating agent, or in combination with magnesium metal in dry ether (Grignard reagent) to form carbon-carbon bonds.
1-Bromobutane may also be used to form organometallic compounds, such as n-butyllithium:[2]
- 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. It can be formed by reaction of butanol with concentrated hydrobromic acid in presence of strong acid, such as sulfuric acid (H2SO4), by reaction of dibutyl ether with hydrobromic acid, or bromination of butane in presence of peroxide.
References
- ↑ "butyl bromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 17 June 2012.
- ↑ Brandsma, L.; Verkraijsse, H. D. (1987). Preparative Polar Organometallic Chemistry I. Berlin: Springer-Verlag. ISBN 3-540-16916-4.