1-Bromobutane is the

organobromine compound Organobromine compounds, also called organobromides, are organic compounds that contain carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons avai ...

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 solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

s. It is a primarily used as a source of the butyl group in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

. 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 In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870. Explanation The rule states that with the addition of a p ...

, i.e. give the 1-bromo derivatives. 1-Bromobutane can also be prepared from

butanol Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4 H9 O H, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a b ...

by treatment with

hydrobromic acid Hydrobromic acid is a strong acid formed by dissolving the diatomic molecule hydrogen bromide (HBr) in water. "Constant boiling" hydrobromic acid is an aqueous solution that distills at and contains 47.6% HBr by mass, which is 8.77 mol/L. H ...

: :CH₃(CH₂)₃OH + HBr → CH₃(CH₂)₃Br + H₂O

Reactions

As a primary

haloalkane The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely us ...

, it is prone to S_N2 type reactions. It is commonly used as an

alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

. When combined with

magnesium Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic ta ...

metal in dry

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

, it gives the corresponding

Grignard reagent A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide ...

. 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.

References

{{DEFAULTSORT:Bromobutane, 1- Bromoalkanes Alkylating agents