1-Bromobutane

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1-Bromobutane

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Template:Longitem	1098260
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MeSH	butyl+bromide
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UN number	1126
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colourless liquid
Density	1.2676 g mL−1
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log P	2.828
Vapor pressure	5.3 kPa
Template:Longitem	140 nmol Pa kg−1
Template:Longitem	1.439
Template:Longitem	162.2 J K−1 mol−1
Template:Longitem	327.02 J K−1 mol−1
Template:Longitem	−148 kJ mol−1
Template:Longitem	−2.7178–−2.7152 MJ mol−1
Flash point	Template:Chembox CalcTemperatures
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Explosive limits	2.8–6.6%
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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.

1-Bromobutane can also be prepared from butanol by treatment with hydrobromic acid:

CH₃(CH₂)₃OH + HBr → CH₃(CH₂)₃Br + H₂O

Reactions

As a primary haloalkane, it is prone to S_N2 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:

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.

1-Fluorobutane can be obtained by reacting 1-bromobutane with potassium fluoride in ethylene glycol.

See also

• 1-Chlorobutane
• 1-Fluorobutane
• 1-Iodobutane