1Chlorobutane

1-chlorobutane, also known as n-butyl chloride, is an organochlorine compound with the formula C4H9Cl. It is a colorless to pale liquid at room temperature and features a primary alkyl chloride, with the chlorine atom attached to the terminal carbon of a four-carbon chain. It is soluble in many organic solvents but has limited miscibility with water.

Production and occurrence

Industrially, 1-chlorobutane is commonly produced by chlorination of n-butane or by conversion of 1-butanol using reagents such as thionyl chloride. It is typically handled and stored under appropriate safety conditions to minimize exposure and degradation.

Physical and chemical properties

1-chlorobutane has a relatively low polarity for an organochlorine compound and is more volatile than longer-chain chlorides. It undergoes typical primary alkyl chloride chemistry: it participates in nucleophilic substitution (SN2) reactions with nucleophiles such as alkoxides, thiolates, cyanide, and amines to form substituted products. It can also hydrolyze in the presence of water and acid or base to yield butanol and hydrochloric acid. The compound is flammable and presents irritation to the skin, eyes, and respiratory tract upon exposure.

Applications and reactions

As a versatile alkylating agent, 1-chlorobutane serves as an intermediate in organic synthesis. It is used to introduce a butyl group into molecules, enabling the formation of butyl ethers, nitriles, and various substituted products. It is employed in the preparation of fragrance and pharmaceutical intermediates, as well as in research and development settings for SN2-type transformations.

Safety and handling

1-chlorobutane should be used in well-ventilated areas, preferably under a fume hood. It is stored in tightly closed containers away from heat, sparks, and oxidizing agents. Adequate personal protective equipment, including gloves and eye protection, is recommended to minimize exposure.