Halohydrin

Halohydrins may be categorized as chlorohydrins, bromohydrins, fluorohydrins or iodohydrins depending on the halogen present.

[4] This reaction is produced on an industrial scale for the production of chlorohydrin precursors to two important epoxides, epichlorohydrin and propylene oxide[citation needed].

Compounds such as 2,2,2-trichloroethanol, which contain multiple geminal halogens adjacent to a hydroxyl group may be considered halohydrins (although, strictly speaking, they fail the IUPAC definition) as they possess similar chemistry.

[8] As with any functional group, the hazards of halohydrins are difficult to generalize as they may form part of an almost limitless series of compounds, with each structure having different pharmacology.

In general, simpler low molecular weight compounds are often toxic and carcinogenic (e.g. 2-chloroethanol, 3-MCPD) by virtue of being alkylating agents.

General structure of a halohydrin, where X = I, Br, F, or Cl
Structure of the halohydrin 2-chloroethanol
Bromohydrin formation
Bromohydrin formation
2,2,2-trichloroethanol