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1-Bromobutane

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1-Bromobutane
Structural formula of 1-bromobutane
Ball-and-stick model
Names
IUPAC name 1-Bromobutane
Other names Butyl bromide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.357 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9Br/c1-2-3-4-5/h2-4H2,1H3Key: MPPPKRYCTPRNTB-UHFFFAOYSA-N
  • InChI=1/C4H9Br/c1-2-3-4-5/h2-4H2,1H3Key: MPPPKRYCTPRNTB-UHFFFAOYAX
SMILES
  • BrCCCC
Properties
Chemical formula C4H9Br
Molar mass 137.020 g·mol
Density 1.2686 g cm, liquid
Melting point −112 °C (−170 °F; 161 K)
Boiling point 101.4 °C (214.5 °F; 374.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1-Bromobutane (CH3(CH2)3Br) is a colorless liquid that is insoluble in water, but soluble in ethanol and diethyl ether. As a primary alkyl halide, 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 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

  1. Brandsma, L.; Verkraijsse, H. D. (1987). Preparative Polar Organometallic Chemistry I. Berlin: Springer-Verlag. ISBN 3-540-16916-4.{{cite book}}: CS1 maint: multiple names: authors list (link)


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